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

Description

Nateglinide Methyl Ester, also known as Nateglinide Methyl Ester Hydrochloride, is a chemical compound derived from nateglinide, a medication used for the treatment of type 2 diabetes. As a prodrug, it is metabolized in the body to release the active form of nateglinide. This white to off-white crystalline powder is soluble in water and ethanol, and is utilized in pharmaceutical research and development to enhance the solubility and bioavailability of nateglinide, thereby increasing its effectiveness in managing diabetes.

Uses

Used in Pharmaceutical Research and Development:
Nateglinide Methyl Ester is used as a prodrug to improve the solubility and bioavailability of nateglinide for better absorption and effectiveness in the treatment of type 2 diabetes.
Used in Diabetes Management:
Nateglinide Methyl Ester is used as a pharmaceutical compound to increase the effectiveness of nateglinide in managing blood sugar levels in patients with type 2 diabetes.
Used in the Development of Improved Formulations:
Nateglinide Methyl Ester is utilized as a key component in the development of new and improved formulations of nateglinide, aiming to enhance the therapeutic outcomes for diabetes management across different patient populations.

Upstream product

• 21685-51-8 D-phenylalanine methyl ester 
• 67-56-1 methanol 
• 7077-05-6 trans-4-isopropylcyclohexane-1-carboxylic acid 
• 673-06-3 D-(R)-phenylalanine 
• 105816-04-4 nateglinide 
• 1245809-48-6 C₁₇H₂₄O₄S 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 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, preferably in b-form

The present invention relates to a process for the preparation of nateglinide, preferably in B-form, substantially free from the H-form, comprising three steps starting from D-phenylalanine methyl ester or a salt thereof.