147650-70-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-Piperazine-2-carboxylic acid is used as a chiral building block for the development of pharmaceuticals, contributing to the creation of enantiomerically pure compounds that are essential for the efficacy and safety of medications.
Used in Agrochemical Production:
In the agrochemical industry, (S)-Piperazine-2-carboxylic acid is utilized as a key intermediate in the synthesis of various agrochemicals, enhancing the selectivity and effectiveness of these products in agricultural applications.
Used in Fine Chemicals Synthesis:
(S)-Piperazine-2-carboxylic acid is employed as a chiral building block in the synthesis of fine chemicals, which are used in a wide range of applications, including fragrances, flavors, and specialty chemicals.
Used in Natural Product Biosynthesis:
(S)-Piperazine-2-carboxylic acid plays a role in the biosynthesis of several natural products, including biologically active alkaloids, which have potential applications in medicine and other fields.
Used in Metabolic Disorders Treatment:
(S)-Piperazine-2-carboxylic acid is being investigated for its potential as a treatment for metabolic disorders, due to its involvement in the biosynthesis of neurotransmitters and other biologically relevant compounds.
Used in Neurodegenerative Disease Research:
L-pipecolic acid is explored for its potential therapeutic applications in neurodegenerative diseases, given its role in neurotransmitter synthesis and its possible impact on disease progression and management.

InChI:InChI=1/C5H10N2O2/c8-5(9)4-3-6-1-2-7-4/h4,6-7H,1-3H2,(H,8,9)/t4-/m0/s1

Upstream product

• 98-96-4 pyrazinamide 
• 84501-64-4 2-aminocarbonylpiperazine 
• 2762-32-5 piperazine-2-carboxylic acid 

Downstream Products

• 138812-69-8 (S)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid 
• 385802-84-6 (S)-4-benzyl 1-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate 
• 1313278-42-0 (S)-4-benzyl 1-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate 
• 138775-03-8 (S)-4-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)-piperazine-2-carboxylic acid 
• 1030377-21-9 (S)-2-(hydroxymethyl)piperazine-1-carboxylic acid tert-butyl ester 
• 848482-93-9 (S)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid 
• 314741-40-7 (3S)-3-(hydroxymethyl)-1-piperazinecarboxylic acid 1,1-dimethylethyl ester 
• 958635-18-2 tert-butyl (8aS)-3-oxotetrahydro-1,3-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate 
• 958635-19-3 1,4-di-tert-butyl 2-methyl (2S)-piperazine-1,2,4-tricarboxylate 

Relevant academic research and scientific papers

Deracemisation and stereoinversion of alpha-amino acids using D-amino acid oxidase and hydride reducing agents.

The deracemisation and stereoinversion of both cyclic and acyclic DL-alpha-amino acids, using porcine kidney D-amino acid oxidase (DAAO) and a hydride reducing agent (NaCNBH3-NaBH4), has been investigated.

Process for the preparation of 2-(S)-piperazinecarboxylic acid by continuous resolution via diastereomeric salt pairs

Continuous resolution of 2-piperazinecarboxylic acid 2 with (S)-camphor-10-sulfonic acid as resolving and epimerisation agent affords 2-(S)-piperazinecarboxylic acid (S)-dicamphor-10-sulfonate 3 in 62% isolated yield and >99% ee.

PROCESS FOR THE PREPARATION OF A CHIRAL PIPERAZINE-2-CARBOXYLIC ACID

The invention relates to a novel process for the preparation of a chiral piperazine-2- carboxylic acid or of a salt thereof of the formula (I). The chiral piperazine-2-carboxylic acid derivatives of the formula (I) are key intermediates for the preparation of fused heteroaryl dihydro pyrimidines which are useful for the treatment and prophylaxis of hepatitis B virus infections.

Preparation of (S)-piperazine-2-carboxylic acid, (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid by kinetic resolution of the corresponding racemic carboxamides with stereoselective amidases in whole bacterial cells

Whole bacterial cells containing stereospecific amidases were used for the kinetic resolution of racemic piperazine-2-carboxamide and piperidine-2-carboxamide to (S)- and (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid, respectively. (S)-Piperazinecarboxylic acid dihydrochloride produced with the biocatalysts Klebsiella terrigena DSM 9174 had an ee value of 99.4% (41% yield), and the ee value of (R)-piperazinecarboxylic acid dihydrochloride obtained with Burkholderia sp. DSM 9925 was 99.0% (22% yield). Using Pseudomonas fluorescens DSM 9924 (S)-piperidine-2-carboxylic acid with an ee value of 97.3% (20% yield) was isolated.