ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate(1206124-13-1) Manufacturer Supplier Exporter Mediocon Inc.
ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate(1206124-13-1) Manufacturer Supplier Exporter Mediocon Inc.
Name: ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate
CAS No: 1206124-13-1 Molecular Weight: 259.31g/mol
Molecular formula
: C15H17NO3
Synonyms-
· Ethyl
1,2,3,4-tetrahydro-7-hydroxycyclopent[b]indole-3-acetate
· 1,2,3,4-Tetrahydro-7-hydroxycyclopent[b]indole-3-acetic
acid ethyl ester
· Cyclopent[b]indole-3-acetic acid,
1,2,3,4-tetrahydro-7-hydroxy-, ethyl ester
· Ethyl
2-{7-hydroxy-1H,2H,3H,4H-cyclopenta[b]indol-3-yl}acetate Appearance: white to light
brown solid
Solubility : soluble in organic
solvents.
Use :
Ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (CAS No.
1206124-13-1) is a specialized organic compound primarily used as a key chemical intermediate in pharmaceutical
research and drug development.
Its most significant role is as a
precursor in the synthesis of Etrasimod
(trade name Velsipity), a medication used to treat autoimmune conditions like
ulcerative colitis.
1. Primary Use: Pharmaceutical
Intermediate
This compound serves as a
"building block" for more complex molecules. Its structural core is
essential for creating drugs that target specific biological pathways.
·
Etrasimod Synthesis: It is an "Impurity" or "Intermediate" (often
referred to as Intermediate 6) in the manufacturing process of Etrasimod.
Etrasimod works as a selective sphingosine-1-phosphate (S1P) receptor
modulator.
·
S1P1 Receptor Agonists: Derivatives of this compound are researched for their ability to
regulate immune cell trafficking, which is crucial for treating autoimmune and inflammatory
disorders like multiple sclerosis and inflammatory bowel disease (IBD).
2. Research & Biological
Activity
In laboratory settings, this specific
molecule is investigated for several potential therapeutic properties:
·
Anti-inflammatory: Studies suggest it may inhibit pro-inflammatory cytokines, making
it a candidate for treating chronic inflammation.
·
Anticancer Potential: Preliminary research has shown it may exhibit cytotoxic effects
against certain cancer cell lines by inducing apoptosis (programmed cell
death).
·
Neuroprotection: There is ongoing interest in its ability to protect neuronal cells
from oxidative stress, which could have implications for neurodegenerative
diseases like Alzheimer's.
3. Chemical Synthesis &
Material Science
·
Chemical Probe: It is used in "Multicomponent Reactions" (MCRs) to create
diverse chemical libraries for drug screening.
·
Advanced Materials: Due to its luminescent properties, it has been explored for
potential use in Organic
Light Emitting Diodes (OLEDs) to improve color range and efficiency.
How is ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate manufactured by Mediocon Inc. Synthesized?
Ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (CAS No. 1206124-13-1) is an essential
pharmaceutical intermediate used in the production of Etrasimod.
While
internal manufacturing records for a specific supplier like Mediocon Inc. are generally
proprietary, companies operating under these standards (WHO-GMP, ISO 9001)
utilize the "telescoped" synthetic pathway first described in the
original drug discovery patents (such as WO2011/094008).
The Core Synthetic Process
The synthesis is a multi-stage
"one-pot" or telescoped procedure that converts a methoxy-precursor
into the final ethyl ester.
Step 1: Demethylation (The
"Deprotection" Phase)
The starting
material is typically 2-(7-methoxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic
acid.
·
Reagent: Boron tribromide (
·
Reaction: The precursor is dissolved in Dichloromethane (
·
Duration: Typically stirred for about 1 hour.
Step 2: Esterification (The "Ester"
Formation Phase)
Rather than isolating the intermediate
hydroxy-acid, the reaction is "telescoped."
·
Reagent: Absolute Ethanol (
·
Reaction: Ethanol is added dropwise to the same reaction vessel while keeping
the temperature below 10°C.
·
Heating: The mixture is then heated (usually to 40°C–60°C) for approximately 30
minutes.
Step
3: Quenching and Neutralization
·
The
reaction is cooled and "quenched" by adjusting the pH.
·
Sodium
Hydroxide (
Purification & Isolation (The
Mediocon Standard)
To achieve the high purity (>98%)
provided by manufacturers like Mediocon, the crude product undergoes rigorous
refining:
1.
Concentration:
Solvents are removed under reduced pressure.
2.
Crystallization: The product is recrystallized. Common solvent systems for this
specific molecule include Ethyl
Acetate/heptanes or Acetonitrile.
3.
Drying: The final light
brown solid is dried under vacuum at ambient temperature to remove residual
solvents.
What are the effects And Side effects of ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate Manufactured by Mediocon Inc. LTD.?
It is important to clarify that Ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate
(manufactured by Mediocon Inc. and others) is a chemical intermediate, not a finished medication.
Consequently, its "effects"
are divided into two categories: its hazards
as a raw chemical (during handling in a lab/factory) and the side effects of the final drug
(Etrasimod) that it is used to create.
1.
Laboratory & Industrial Effects (Safety Data)
If you are handling this substance as a
chemical professional, the primary effects are related to physical contact and
inhalation. According to the Material Safety Data Sheet (MSDS):
·
Skin Irritation: May cause redness and discomfort
if it comes into contact with the skin.
·
Eye Irritation:
Causes significant eye irritation; direct contact can lead to stinging and
watering.
·
Respiratory
Irritation: If inhaled as a dust or powder, it may
irritate the nose, throat, and lungs, causing coughing or shortness of breath.
·
Acute
Toxicity: While not classified as highly toxic, it
should not be ingested. In laboratory models, high
doses can cause somnolence (drowsiness
or depressed activity).
Handling
Precautions
Manufacturers like Mediocon recommend
the following protective measures:
·
Gloves and Safety Goggles: To prevent skin and eye exposure.
·
Ventilation: Use in a chemical fume hood to avoid inhaling dust.
·
Storage: Keep at 2–8°C in a tightly sealed container,
protected from light.
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2.
Side Effects of the Final Product (Etrasimod)
Because this chemical is the primary
"building block" for Etrasimod
(Velsipity), the clinical side effects associated with the finished drug
are often researched in connection with this molecule. Once synthesized into
Etrasimod and taken by patients (e.g., for Ulcerative Colitis), the following
side effects may occur:
How is ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate Manufactured by Mediocon Inc. Tested Qualitatively?
In pharmaceutical manufacturing, companies like Mediocon Inc. perform qualitative
testing to confirm the identity and purity of a substance before it is used to
synthesize a final drug (like Etrasimod).
For Ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate,
qualitative testing ensures that the "building block" has been
constructed correctly.
1. Primary Qualitative
Identification Methods
Because this molecule is an indole
derivative, specialized laboratory techniques are used to
"fingerprint" it.
·
Proton Nuclear Magnetic Resonance ($^1H\text{ NMR}$):
This is the most definitive qualitative test. It maps the hydrogen atoms in the
molecule. For this specific compound, chemists look
for the "signature" peaks of the indole NH group (typically around
·
LC-MS
(Liquid Chromatography-Mass Spectrometry): This test
confirms the "Molecular Weight." Since this
compound has a molecular weight of 259.31
g/mol, a positive qualitative test will show a peak at
·
FT-IR
Spectroscopy (Fourier-Transform Infrared): This
identifies the functional groups. A successful test will show a strong
"stretch" at approximately $1730\text{ cm}^{-1}$, confirming
the presence of the ester ($C=O$)
group, and a broad peak around $3400\text{
cm}^{-1}$ for the hydroxyl
($-OH$)
group.
2. Physical Qualitative Checks
Before chemical analysis, basic
physical properties are verified against the manufacturer's Certificate of
Analysis (CoA):
·
Appearance: Verified
as a white to light brown solid.
·
Solubility: Tested qualitatively by ensuring the powder dissolves completely in
solvents like Dichloromethane ($CH_2Cl_2$)
or Ethyl Acetate, but remains
insoluble in water.
·
Melting Point: A small sample is heated; if the
substance is pure and correctly identified, it will melt within a very narrow,
specific temperature range (typically noted on the batch-specific CoA).
3. Purity & Impurity Screening
While "qualitative" usually
means what it is, in the
pharmaceutical industry, it also includes identifying what it isn't:
·
Thin-Layer Chromatography (TLC): A quick
"spot test" to ensure only one major dot appears on the plate. If a
second dot appears, it indicates a qualitative failure due to the presence of
an unreacted intermediate (like the methoxy precursor).
·
HPLC Retention Time: In a standard test, the
sample is run through an HPLC machine. If its "retention time" (the
time it takes to travel through the machine) matches a known standard of the
compound, the identity is confirmed.
Which tests are performed on ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate Manufactured
Mediocon Inc. LTD.?
In the pharmaceutical industry, companies like Mediocon Inc. LTD. perform a specific
battery of tests on Ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (CAS
1206124-13-1) to ensure it meets the rigid specifications required for Etrasimod
synthesis.
These tests are divided into three main
categories: Identification, Purity/Assay, and Physical Characterization.
1. Identity Verification (Is it the right
molecule?)
These tests "fingerprint" the
chemical structure to confirm that the synthesis was successful.
·
Proton NMR ($^1H\text{-NMR}$):
The gold standard for confirming the molecular skeleton. Analysts look for
specific signals, such as the NH
singlet around $\delta\text{ 10.25 ppm}$ and the ethyl quartet/triplet characteristic
of the acetate group.
·
LC-MS (Mass Spectrometry): Confirms the molecular
weight. For this compound, the test must show a dominant peak at $m/z = 260.1$ ($M+H$).
·
FT-IR (Infrared Spectroscopy): Used to verify
functional groups. A peak at approximately $1730\text{ cm}^{-1}$ confirms the
ester bond ($C=O$),
and a broad peak near $3400\text{
cm}^{-1}$ confirms the hydroxyl group ($-OH$).
2. Purity and Assay (How clean is it?)
These tests determine the concentration
of the actual chemical versus impurities or leftover reagents.
·
HPLC (High-Performance Liquid Chromatography):
Used to determine the Assay percentage.
Mediocon typically guarantees a purity of $\ge$ 98% or 99%. HPLC also identifies
"related substances" (impurities from the manufacturing process).
·
Chiral HPLC: Since Etrasimod requires a specific
orientation (the R-isomer), this
test is performed to check the Enantiomeric
Excess (ee).
·
Loss on Drying (LOD): Measures the amount of
water or volatile solvents remaining in the powder.
·
Residue on Ignition (ROI): Checks for inorganic
impurities (like metal catalysts) left over from the synthesis.
3. Physical & Safety Testing
·
Appearance: A visual
check to confirm the product is a white
to light brown solid/powder.
·
Solubility: Qualitative check to ensure the compound dissolves in expected
solvents like DMSO or Methanol but is nearly insoluble in
water.
·
Melting Point: Verified using a capillary tube; a
sharp melting range indicates high purity.
·
Heavy Metals: Inductively Coupled Plasma (ICP)
testing is often used to ensure the sample is free from toxic metals like Lead
or Arsenic.
What are the challenges in Manufacturing of ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate Intermediate Manufactured
by Mediocon Inc. LTD?
Manufacturing Ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate at a
commercial scale, such as by Mediocon
Inc. LTD, involves several technical and chemical hurdles. Because this
compound is a critical intermediate for the drug Etrasimod, maintaining high purity while managing volatile
reactions is the primary focus.
The main challenges include:
1. Handling Highly Reactive & Hazardous
Reagents
The synthesis
typically requires Boron tribromide (
·
Challenge: $BBr_3$
is extremely corrosive, toxic, and reacts violently with water/moisture to
release hydrogen bromide gas.
·
Manufacturing Impact: This requires specialized
"Glass-Lined Reactors" (GLR) and strict moisture-free environments
(nitrogen blanketing) to prevent equipment corrosion and safety hazards.
2. Precise Cryogenic Temperature Control
The reaction
with
·
Challenge: The demethylation must be performed at cryogenic temperatures (between
·
Manufacturing
Impact: If the temperature rises even slightly, it can
lead to side reactions, such as the degradation of the indole ring or unwanted
bromination, which significantly lowers the purity of the final batch.
3. Regioselectivity and Structural
Sensitivity
The indole nucleus is
"electron-rich," meaning it is prone to reacting at the wrong
positions.
·
Challenge: Ensuring the 7-hydroxy group is
correctly exposed without affecting the cyclopentane ring or the acetate chain.
·
Manufacturing Impact: Side products (isomers) are
difficult to remove because they have physical properties very similar to the
target molecule. This often necessitates expensive and time-consuming
recrystallization steps to achieve the $>98\%$ purity standard.
4. Stability and Storage Issues
Indole derivatives, especially those
with a free hydroxyl ($-OH$) group like this intermediate, are
sensitive to environmental factors.
·
Challenge: The compound
is hygroscopic (absorbs moisture
from the air) and light-sensitive.
·
Manufacturing
Impact: It must be stored in
specialized amber-colored containers under an inert gas (Argon or Nitrogen) and
kept in cold storage (
5.
Managing the "Telescoped" Process
Manufacturers like Mediocon often use
a "one-pot" or telescoped method where the demethylation and
esterification happen in sequence without isolating the middle product.
·
Challenge: Any leftover $BBr_3$ or acid from the
first step can interfere with the ethanol used in the second step
(esterification).
·
Manufacturing Impact: This requires a very
precise "quenching" and pH adjustment (usually to $pH\text{
}7\text{--}8$) to ensure the reaction moves forward efficiently
without destroying the delicate ester bond.
What is the Packing for ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate Manufactured
by Mediocon Inc.. LTD.?
In the pharmaceutical industry, packaging for intermediates
like Ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (manufactured
by companies like Mediocon Inc. LTD)
is designed to protect the chemical from moisture, light, and oxidation while
ensuring safety during bulk transport.
For a commercial-scale manufacturer,
the packaging typically follows these standards:
1. Bulk Commercial Packaging
For industrial or large-scale synthesis
of Etrasimod, the standard package size is:
·
Standard Unit: 25 kg per Fiber Drum.
·
Inner
Lining: The compound is typically contained within double-layered Anti-static Polyethylene (PE)
bags. These bags are vacuum-sealed or tied securely to prevent the
"hygroscopic" (moisture-absorbing) powder from clumping.
·
Tamper Evidence: Drums are often fitted with
security seals and include a moisture-absorbing silica gel desiccant pack
between the two bags.
2. Research & Laboratory Packaging
If the compound is being supplied in
smaller quantities for R&D purposes, it is packed as follows:
·
Sizes: 100 mg, 1 g, 10 g, or 1 kg.
·
Container: Amber glass bottles or high-density polyethylene (HDPE) bottles.
Amber glass is used specifically because this indole intermediate is light-sensitive and can degrade if
exposed to UV rays.
·
Atmosphere: Often sealed under an Inert Gas (such as Nitrogen or Argon)
to prevent oxidation of the 7-hydroxy group.
3. Labeling and Documentation
Every package from Mediocon Inc. will
include specific regulatory labeling:
·
Batch/Lot Number: For traceability.
·
Storage Instructions: Clearly marked "Store at 2–8°C" or "Store in a cool, dry place".
·
Hazard Symbols: GHS pictograms for
"Irritant" (Exclamation Mark) and "Health Hazard" if
applicable.
·
Documentation: A Certificate of Analysis (CoA) and Material Safety Data Sheet (MSDS) are included in a waterproof
pouch on the outside of the drum.
What is shelf life Of ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate Manufactured by Mediocon Inc.. LTD.?
The standard shelf life for Ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate
(CAS No. 1206124-13-1) manufactured by companies like Mediocon Inc. LTD. is generally 2 years (24 months) from the date of
manufacture.
To
maintain this shelf life and ensure the chemical purity remains above the
required 98%, the following storage conditions must be strictly followed:
1. Temperature Control
·
Recommended Storage: 2°C to 8°C (Refrigerated).
·
Reasoning: Indole derivatives are sensitive to thermal degradation. Storing
them at room temperature for extended periods can lead to the formation of
impurities, which would fail a retest for pharmaceutical use.
2. Environmental Protection
·
Light Sensitivity: The compound must be stored in
amber-colored containers or
opaque drums. Exposure to light can cause the powder to darken (oxidize),
indicating chemical breakdown.
·
Atmospheric Conditions: It is typically sealed under an Inert Gas (such as Nitrogen or Argon).
·
Moisture
(Hygroscopy): The compound is hygroscopic, meaning it
absorbs moisture from the air.
3.
Retest Period
In a GMP (Good Manufacturing Practice)
environment, even if the shelf life is listed as 2 years, manufacturers often
assign a Retest Date at the 12-month mark.
·
If the chemical is still in its
original, unopened packaging, it is re-tested via HPLC.
·
If it passes the purity
specifications (typically $>98\%$), its use-life can be extended
for an additional period (usually 6 to 12 months).
Where can ethyl
2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate Manufactured by Mediocon Inc. LTD. are procured?
ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate Manufactured by Mediocon
Inc. can be procured from various sources, depending on your location and
requirements. Here are some options:
FOR API INTERMEDIATES
Mediocon Inc. Plot No D 187/16 Five
Star MIDC, Shendra, Aurangabad-431154, Aurangabad, Maharashtra, India
Mob/Whatsapp No: +91-9403003010, +91-9420294801
Sales Department: Email: sales@internediates.ai
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