181289-34-9

Basic information

• Product Name: Hexanoicacid, 3-(2-amino-2-oxoethyl)-5-methyl-, (3S)-
• Synonyms: Hexanoicacid, 3-(2-amino-2-oxoethyl)-5-methyl-, (S)- (9CI)
• CAS NO: 181289-34-9
• Molecular Formula: C9H17 N O3
• Molecular Weight: 187.239
• Mol File: 181289-34-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Hexanoicacid, 3-(2-amino-2-oxoethyl)-5-methyl-, (3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Hexanoicacid, 3-(2-amino-2-oxoethyl)-5-methyl-, (3S)-(181289-34-9)
• EPA Substance Registry System: Hexanoicacid, 3-(2-amino-2-oxoethyl)-5-methyl-, (3S)-(181289-34-9)

Safety Data

• Hazardous Substances Data: 181289-34-9(Hazardous Substances Data)

Usage

General Description

Hexanoic acid, 3-(2-amino-2-oxoethyl)-5-methyl-, (3S)- is a chemical compound consisting of a six-carbon chain with a carboxylic acid group and a 3-(2-amino-2-oxoethyl)-5-methyl side chain. It is commonly known as L-leucine, which is an essential amino acid that is important for protein synthesis and muscle growth. L-leucine plays a crucial role in promoting muscle recovery and preventing muscle protein breakdown during exercise. It is also involved in the regulation of blood sugar levels and energy production in the body. L-leucine can be found in various foods such as meat, dairy products, and legumes, and is also available as a dietary supplement for athletes and individuals looking to improve their muscle mass and athletic performance.

Upstream product

• 181289-15-6 (±)?3?(carbamoylmethyl)?5?methylhexanoic acid 
• 181289-25-8 (3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid 
• 1231239-92-1 C₂₀H₃₀O₃S 

Downstream Products

• 75143-89-4 5-methyl-3-carboxymethylhexanoic acid 
• 181289-33-8 (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid 
• 181289-15-6 (±)?3?(carbamoylmethyl)?5?methylhexanoic acid 
• 148553-50-8 pregabilin 

Relevant articles and documents

Development of a new synthesis approach for S-pregabalin by optimizing the preparation stages

In the present study, we aimed to optimize the synthesis stages of S-pregabalin ((S)-3-(aminomethyl)-5-methylhexanoic acid), a well-known anticonvulsant drug. We used appropriate solvents and compounds to reach a straightforward and applicable method. The advantages of this research were avoiding use of expensive and environment pollutant reagents and solvents, and also using a recoverable reagent. Discarding prevention of the intermediates and reagents besides attaining a higher yield of the obtained product were the additional achievements. All structures were characterized by FT-IR, 1H NMR, and the purity of S-pregabalin was evaluated using the HPLC assay.

Synergistic organocatalysis in the kinetic resolution of secondary thiols with concomitant desymmetrization of an anhydride

Kinetic resolution is an important method for the separation of racemates into their component enantiomers. Thiols are precursors to a variety of organosulfur compounds, with high utility in both chemistry and chemical biology, yet there is a surprising dearth of methodologies for their direct and efficient catalytic kinetic resolution. Here, we demonstrate an organocatalytic process involving the highly enantioselective desymmetrization of an achiral electrophile with the simultaneous kinetic resolution of a racemic thiol. The preparative potential of the methodology is exemplified by the synthesis of a drug precursor antipode in excellent yield and enantioselectivity as a by-product of a process that also resolves a sec-thiol substrate with a selectivity of S = 226 (that is, both thiol antipodes produced in 95% ee at 51% conversion). In a second example a racemic sec-thiol representing the stereocentre-containing core of the anti-asthma drug (R)-Montelukast was resolved with synthetically useful selectivity under mild conditions.

An efficient process of racemization of 3-(Carbamoylmethyl)-5- methylhexanoic acid: A pregabalin intermediate

A simple and cost-effective process for racemization of undesired (S)-3-(carbamoylmethyl)-5-methylhexanoic acid (9), produced during the resolution step, is described. The literature procedure is fraught with many difficulties including number of steps and hazardous reagents. We have developed a one pot process for the above-mentioned racemization of S-enantiomer. The basic objective is to convert S-enantiomer into the symmetrical glutarimide derivative followed by hydrolysis with an alkali. The transformation of 9 into glutarimide derivative (10) has been achieved with piperidine in refluxing toluene.