(S)-Piperazine-2-carboxylic acid

Base Information

• Chemical Name: (S)-Piperazine-2-carboxylic acid
• CAS No.: 147650-70-2
• Molecular Formula: C5H10N2O2
• Molecular Weight: 130.1451
• Hs Code.: 2933599090
• DSSTox Substance ID: DTXSID40363601
• Nikkaji Number: J673.453G
• Wikidata: Q72500010
• Metabolomics Workbench ID: 58810
• ChEMBL ID: CHEMBL1229074
• Mol file: 147650-70-2.mol

Synonyms:(S)-(-)piperazine-2-carboxylic acid;piperazine-2-carboxylic acid

Chemical Property of (S)-Piperazine-2-carboxylic acid

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 0.000107mmHg at 25°C
• Melting Point: 243-247 °C (dec.)
• Refractive Index: 1.476
• Boiling Point: 313.6 °C at 760 mmHg
• PKA: 1.90±0.20(Predicted)
• Flash Point: 143.5 °C
• PSA: 61.36000
• Density: 1.174 g/cm³
• LogP: -0.71000
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 130.074227566
• Heavy Atom Count: 9
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

(S)-Piperazine-2-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(CN1)C(=O)O
• Isomeric SMILES: C1CN[C@@H](CN1)C(=O)O

Technology Process of (S)-Piperazine-2-carboxylic acid

There total 3 articles about (S)-Piperazine-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

piperazine-2-carboxylic acid (2762-32-5) → (2S)-piperazine-2-carboxylic acid (147650-70-2)

Guidance literature:

With porcine kidney D-amino acid oxidase (EC 1.4.3.3.); sodium cyanoborohydride; flavin adenine dinucleotide; In phosphate buffer; at 37 ℃;

DOI:10.1039/b107580m

Reference yield:

2-aminocarbonylpiperazine (84501-64-4) → (2S)-piperazine-2-carboxylic acid (147650-70-2)

Guidance literature:

With air; Klebsiella terrigena DSM 9174 cells; glycerol; yeast extract; at 40 - 47 ℃;

DOI:10.1016/S0957-4166(97)00256-5

Reference yield:

pyrazinamide (98-96-4) → (2S)-piperazine-2-carboxylic acid (147650-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 82.2 percent / H₂ / 10percent Pd/C / ethanol / 5 h / 85 °C / 15001.2 Torr

2: Klebsiella terrigena DSM 9174 cells, yeast extract, glycerine, air / 40 - 47 °C

With air; Klebsiella terrigena DSM 9174 cells; hydrogen; glycerol; yeast extract; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0957-4166(97)00256-5

upstream raw materials:

piperazine-2-carboxylic acid

2-aminocarbonylpiperazine

pyrazinamide

Downstream raw materials:

(S)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid

(S)-4-benzyl 1-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate

(S)-4-benzyl 1-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate

(S)-4-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)-piperazine-2-carboxylic acid

Refernces

• 1、 Stingl, Klaus,Kottenhahn, Matthias,Drauz, Karlheinz. "Process for the preparation of 2-(S)-piperazinecarboxylic acid by continuous resolution via diastereomeric salt pairs". . p. 979 - 982. Retrieved 1997.
• 2、 Eichhorn, Eric,Roduit, Jean-Paul,Shaw, Nicholas,Heinzmann, Klaus,Kiener, Andreas. "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". . p. 2533 - 2536. Retrieved 2007/10/03.