Repaglinide ethyl ester

Cat. No.: B8791419

M. Wt: 480.6 g/mol

InChI Key: FTCMVLQJMIXDSI-UHFFFAOYSA-N

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Overview

1. Description

7. Properties

2. Preparation methods

8. Synthesis routes and methods I

3. Chemical reactions analysis

9. Synthesis routes and methods II

4. Scientific research applications

10. Synthesis routes and methods III

5. Mechanism of action

11. Disclaimer

6. Comparison with similar compounds

Description

Repaglinide ethyl ester is a chemical compound that serves as an intermediate in the synthesis of repaglinide, a medication used to manage type 2 diabetes mellitus. Repaglinide is a non-sulfonylurea insulin secretagogue that helps regulate blood glucose levels by stimulating insulin release from pancreatic beta cells .

Preparation Methods

Synthetic Routes and Reaction Conditions

Repaglinide ethyl ester can be synthesized through various synthetic routes. One common method involves the esterification of 3-hydroxyphenylacetic acid, followed by formylation, oxidation, etherification, and selective hydrolysis . The reaction conditions, such as temperature, time, solvent, and substrate ratios, are optimized to achieve high yields and purity .

Industrial Production Methods

In industrial settings, the production of this compound involves large-scale synthesis using similar reaction steps. The process is designed to be scalable and environmentally friendly, minimizing waste and optimizing resource utilization .

Chemical Reactions Analysis

Types of Reactions

Repaglinide ethyl ester undergoes various chemical reactions, including:

Oxidation: Conversion of functional groups to higher oxidation states.

Reduction: Conversion of functional groups to lower oxidation states.

Substitution: Replacement of one functional group with another.

Common Reagents and Conditions

Common reagents used in these reactions include oxidizing agents like potassium permanganate, reducing agents like lithium aluminum hydride, and substitution reagents like ethyl bromide . The reactions are typically carried out under controlled conditions to ensure high selectivity and yield.

Major Products Formed

The major products formed from these reactions include various intermediates that are further processed to produce repaglinide .

Scientific Research Applications

Repaglinide ethyl ester has several scientific research applications:

Chemistry: Used as an intermediate in the synthesis of repaglinide and other related compounds.

Biology: Studied for its role in modulating insulin release and its potential effects on pancreatic beta cells.

Medicine: Essential in the development of repaglinide, a drug used to manage type 2 diabetes mellitus.

Industry: Utilized in the large-scale production of repaglinide, ensuring consistent quality and supply.

Mechanism of Action

Repaglinide ethyl ester itself does not have a direct mechanism of action, as it is an intermediate compound. repaglinide, the final product, exerts its effects by inhibiting ATP-sensitive potassium channels in pancreatic beta cells. This inhibition leads to membrane depolarization, opening of calcium channels, and subsequent insulin release .

Comparison with Similar Compounds

Similar Compounds

Similar compounds to repaglinide ethyl ester include:

Nateglinide: Another meglitinide class drug used to manage type 2 diabetes.

Mitiglinide: A similar insulin secretagogue with a different chemical structure.

Uniqueness

This compound is unique due to its specific role as an intermediate in the synthesis of repaglinide. Its optimized synthetic route and reaction conditions make it a valuable compound in the pharmaceutical industry .

Properties

Molecular Formula	C29H40N2O4
Molecular Weight	480.6 g/mol
IUPAC Name	ethyl 2-ethoxy-4-[2-[[3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoate
InChI	InChI=1S/C29H40N2O4/c1-5-34-27-19-22(14-15-24(27)29(33)35-6-2)20-28(32)30-25(18-21(3)4)23-12-8-9-13-26(23)31-16-10-7-11-17-31/h8-9,12-15,19,21,25H,5-7,10-11,16-18,20H2,1-4H3,(H,30,32)
InChI Key	FTCMVLQJMIXDSI-UHFFFAOYSA-N
Canonical SMILES	CCOC1=C(C=CC(=C1)CC(=O)NC(CC(C)C)C2=CC=CC=C2N3CCCCC3)C(=O)OCC
Origin of Product	United States

Synthesis routes and methods I

Procedure details

Prepared from ethyl 2-ethoxy-4-[N-{1-(2-piperidino-phenyl)-3-methyl-1-buten-1-yl}-aminocarbonylmethyl]-benzoate, melting point 125°-126° C., which in turn was prepared from (2-piperidino-phenyl)-isobutyl-ketimine and 3-ethoxy-4-ethoxy-carbonyl-phenol-acetic acid analogous to Example 1.

Name

ethyl 2-ethoxy-4-[N-{1-(2-piperidino-phenyl)-3-methyl-1-buten-1-yl}-aminocarbonylmethyl]-benzoate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

[Compound]

Name

(2-piperidino-phenyl)-isobutyl-ketimine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

3-ethoxy-4-ethoxy-carbonyl-phenol acetic acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

Ethyl 2-ethoxy-4-[N-{1-(2-piperidino-phenyl)-3-methyl-1-butyl}-aminocarbonylmethyl]-benzoate

Details

Synthesis routes and methods II

Procedure details

3 g (11.9 mmols) of 3-ethoxy-4-ethoxycarbonylphenylacetic acid, 3.7 g (14.3 mmols) of triphenylphosphine, 3.3 ml (23.8 mmols) of triethylamine and 1.15 ml (11.9 mmols) of carbon tetrachloride were added successively to a solution of 2.9 g (11.9 mmols) of 3-methyl-1-(2-piperidino-phenyl)-1-butylamine in 29 of acetonitrile. The mixture was then stirred for 15 hours at room temperature, the solvent was removed in vacuo, and the residue was taken up in a mixture of ethyl acetate and water. The organic phase was dried over sodium sulfate, filtered and concentrated by evaporation in vacuo. The evaporation residue was purified by column chromatography on silaca gel (toluene/acetone=10/1).

Name

3-ethoxy-4-ethoxycarbonylphenylacetic acid

Quantity

3 g

Type

reactant

Reaction Step One

Name

triphenylphosphine

Quantity

3.7 g

Type

reactant

Reaction Step One

Name

triethylamine

Quantity

3.3 mL

Type

reactant

Reaction Step One

Name

carbon tetrachloride

Quantity

1.15 mL

Type

reactant

Reaction Step One

Name

3-methyl-1-(2-piperidino-phenyl)-1-butylamine

Quantity

2.9 g

Type

reactant

Reaction Step One

Name

acetonitrile

Quantity

0 (± 1) mol

Type

solvent

Reaction Step One

Name

Ethyl 2-ethoxy-4-[N-{1-(2-piperidino-phenyl)-3-methyl-1-butyl}-aminocarbonylmethyl]-benzoate

Details

Synthesis routes and methods III

Procedure details

Prepared from (S)-3-Methyl-1-(2-piperidino-phenyl)-1-butylamine and 3-ethoxy-4-ethoxycarbonyl-phenylacetic acid analogously to Example 1.

Name

(S)-3-Methyl-1-(2-piperidino-phenyl)-1-butylamine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

3-ethoxy-4-ethoxycarbonyl-phenylacetic acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

Ethyl 2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl]benzoate

Details

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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.

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