(2S)-2-(6-chloro-9H-carbazol-2-yl)propanoic acid

Base Information

• Chemical Name: (2S)-2-(6-chloro-9H-carbazol-2-yl)propanoic acid
• CAS No.: 52263-84-0
• Molecular Formula: C15H12ClNO2
• Molecular Weight: 273.71
• DSSTox Substance ID: DTXSID70349877
• Wikidata: Q27126533
• Metabolomics Workbench ID: 60473
• ChEMBL ID: CHEMBL2171249
• Mol file: 52263-84-0.mol

Synonyms:(S)-Carprofen;(+)-carprofen;(2S)-2-(6-chloro-9H-carbazol-2-yl)propanoic acid;52263-84-0;(S)-(+)-carprofen;CHEMBL2171249;CHEBI:59207;(S)-2-(6-Chloro-9H-carbazol-2-yl)propanoic acid;(S)-6-chloro-alpha-methylcarbazole-2-acetic acid;(S)-2-(3-chloro-9H-carbazol-7-yl)propanoic acid;(S)-2-(6-chloro-9H-carbazol-2-yl)-propionic acid;4mjr;0LA;S)-(+)-carprofen;4do3;SCHEMBL3698103;DTXSID70349877;BDBM50397558;CS-0529283;A16428;Q27126533

Chemical Property of (2S)-2-(6-chloro-9H-carbazol-2-yl)propanoic acid

Chemical Property:

• PSA: 53.09000
• LogP: 4.16260
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 273.0556563
• Heavy Atom Count: 19
• Complexity: 362

Purity/Quality:

99.3% ^*data from raw suppliers

(S)-Carprofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC2=C(C=C1)C3=C(N2)C=CC(=C3)Cl)C(=O)O
• Isomeric SMILES: C[C@@H](C1=CC2=C(C=C1)C3=C(N2)C=CC(=C3)Cl)C(=O)O
• Uses: The S-enantiomer of the antiinflammatory drug Carprofen

Technology Process of (2S)-2-(6-chloro-9H-carbazol-2-yl)propanoic acid

There total 14 articles about (2S)-2-(6-chloro-9H-carbazol-2-yl)propanoic 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:

(2S)-(6-chloro-9-(4-chlorobenzoyl)-9H-carbazol-2-yl)propanoic acid (1402840-99-6) → (S)-carprofen (52263-84-0,52263-83-9)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 40 ℃; for 72h;

DOI:10.1021/jm3011146

Reference yield:

(2S)-(6-chloro-9-(oxazol-4-ylcarbonyl)-9H-carbazol-2-yl)propanoic acid (1402841-01-3) → (S)-carprofen (52263-84-0,52263-83-9)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 40 ℃; for 72h;

DOI:10.1021/jm3011146

Reference yield:

ethyl 2-(6-chloro-9H-carbazol-2-yl)propanoate (52262-89-2) → (S)-carprofen (52263-84-0,52263-83-9) + (R)-6-chloro-α-methyl-carbazole-2-acetic acid (52263-83-9)

Guidance literature:

With esterase variant Est_{816A216F/F142Y/A149L/K238N}; In aq. phosphate buffer; dimethyl sulfoxide; at 40 ℃; enantioselective reaction; Enzymatic reaction;

DOI:10.1039/d1cy01028j

upstream raw materials:

2-(6-chloro-carbazol-2-yl)-propionic acid

benzyl 2-(6-chloro-9-(4-chlorobenzoyl)-9H-carbazol-2-yl)-propanoate

benzyl 2-(6-chloro-9-(oxazol-4-ylcarbonyl)-9H-carbazol-2-yl)propanoate

(2S)-(6-chloro-9-(4-chlorobenzoyl)-9H-carbazol-2-yl)propanoic acid

Refernces

• 1、 Yuan, Xin,Liu, Guangyong,Zhang, Panliang,Xu, Weifeng,Tang, Kewen. "Lipase-Catalyzed Production of (S)-Carprofen Enhanced by Hydroxyethyl-β-cyclodextrins: Experiment and Optimization". . p. 891 - 899. Retrieved 2019/05/01.
• 2、 Kucerova, Gabriela,Kalikova, Kveta,Tesarova, Eva. "Enantioselective potential of polysaccharide-based chiral stationary phases in supercritical fluid chromatography". supporting information. p. 239 - 246. Retrieved 2017/05/29.