105746-47-2

Basic information

• Product Name: Nateglinide Methyl Ester
• Synonyms: Nateglinide Methyl Ester;Nateglinide Impurity;(R)-methyl 2-((1r,4R)-4-isopropylcyclohexanecarboxamido)-3-phenylpropanoate
• CAS NO: 105746-47-2
• Molecular Formula: C₂₀H₂₉NO₃
• Molecular Weight: 331.44916
• Mol File: 105746-47-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Nateglinide Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: Nateglinide Methyl Ester(105746-47-2)
• EPA Substance Registry System: Nateglinide Methyl Ester(105746-47-2)

Safety Data

• Hazardous Substances Data: 105746-47-2(Hazardous Substances Data)

Usage

General Description

Nateglinide Methyl Ester, also known as Nateglinide Methyl Ester Hydrochloride, is a chemical compound that is a derivative of nateglinide, a drug used in the treatment of type 2 diabetes. Nateglinide Methyl Ester is a prodrug, meaning that it is metabolized in the body to produce the active form of nateglinide. Nateglinide Methyl Ester is a white to off-white crystalline powder that is soluble in water and ethanol. It is used in pharmaceutical research and development to improve the solubility and bioavailability of nateglinide, and to increase its effectiveness in the treatment of diabetes. Nateglinide Methyl Ester has potential applications in the development of new and improved formulations of nateglinide for the management of diabetes.

Upstream product

• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 21685-51-8 D-phenylalanine methyl ester 
• 1245809-48-6 C₁₇H₂₄O₄S 
• 67-56-1 methanol 
• 7077-05-6 trans-4-isopropylcyclohexane-1-carboxylic acid 
• 673-06-3 D-(R)-phenylalanine 
• 105816-04-4 nateglinide 
• 175284-00-1 p-menthan-7-oic acid methyl ester 

Downstream Products

• 594837-85-1 C₁₉H₂₆NO₃^(1-)*Na⁽¹⁺⁾ 
• 594837-86-2 C₁₉H₂₆NO₃^(1-)*K⁽¹⁺⁾ 
• 105816-04-4 nateglinide 

Relevant articles and documents

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

A PROCESS FOR THE PREPARATION OF NATEGLINIDE

The present invention relates to a process for the preparation of substantially pure nateglinide of formula (I), substantially free from the cis-isomer and L-enantiomer and preparation of enantiomerically pure nateglinide form B, directly from the hydrolysis of a (-)-N-(trans-4-isopropylcyclohexyl-1-carbonyl)-D-phenylalanine alkyl ester in a ketonic solvent or water or mixture thereof.

PROCESS FOR THE PREPARATION OF NATEGLINIDE

One-pot process for the preparation of nateglinide, which process comprises reacting an alkyl ester of D-phenylalanine of formula (II) where R represents C1-4alkyl, typically methyl, either as the free base or in salt form (typically the hydrochloride), with trans-4-isopropylcyclohexanecarboxylic acid of formula (III) where X represents hydroxy or halo, typically chloro, to obtain a C1-4 alkyl ester of nateglinide of formula (IV), preferably the methyl ester of nateglinide followed by hydrolysis to yield nateglinide of formula (I).