(R)-Carprofen

Base Information

• Chemical Name: (R)-Carprofen
• CAS No.: 52263-83-9
• Molecular Formula: C₁₅H₁₂ClNO₂
• Molecular Weight: 273.719
• DSSTox Substance ID: DTXSID40426422
• Wikidata: Q27126532
• Metabolomics Workbench ID: 60472
• ChEMBL ID: CHEMBL2171250
• Mol file: 52263-83-9.mol

Synonyms:(R)-Carprofen;(-)-carprofen;52263-83-9;(2R)-2-(6-chloro-9H-carbazol-2-yl)propanoic acid;(R)-(-)-carprofen;CHEMBL2171250;CHEBI:59206;(R)-6-chloro-alpha-methylcarbazole-2-acetic acid;(R)-2-(6-Chloro-9H-carbazol-2-yl)propanoic acid;(R)-2-(3-chloro-9H-carbazol-7-yl)propanoic acid;(R)-2-(6-chloro-9H-carbazol-2-yl)-propionic acid;SCHEMBL3910;9H-Carbazole-2-acetic acid, 6-chloro-.alpha.-methyl-, (.alpha.R)-;DTXSID40426422;PUXBGTOOZJQSKH-MRVPVSSYSA-N;BDBM50397557;PD132828;CS-0529281;Q27126532;UHG

Chemical Property of (R)-Carprofen

Chemical Property:

• 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

(R)-Carprofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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 R-enantiomer of the antiinflammatory drug Carprofen

Technology Process of (R)-Carprofen

There total 88 articles about (R)-Carprofen 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: 92.0%

methyl 9-benzoyl-2-(6-chlorocarbazol-2-yl)propanoate → 2-(6-chloro-carbazol-2-yl)-propionic acid (53716-49-7,52263-83-9)

Guidance literature:

With sodium hydroxide; In methanol; at 80 ℃; for 1.5h;

DOI:10.1002/chem.202003430

Reference yield: 91.0%

2-(3-((4-chlorophenyl)amino)-4-chlorophenyl)propanoic acid → 2-(6-chloro-carbazol-2-yl)-propionic acid (53716-49-7,52263-83-9)

Guidance literature:

With triphenylphosphine; palladium dichloride; sodium t-butanolate; In N,N-dimethyl-formamide; at 100 ℃; for 10h; Reagent/catalyst; Inert atmosphere;

Reference yield: 91.0%

ethyl 2-(6-chloro-9H-carbazol-2-yl)propanoate (52262-89-2) → 2-(6-chloro-carbazol-2-yl)-propionic acid (53716-49-7,52263-83-9)

Guidance literature:

With water; sodium hydroxide; In methanol; at 20 ℃; for 8h; Inert atmosphere; Schlenk technique;

upstream raw materials:

methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate

2-(1-cyanoethyl)-6-chlorocarbazole

2-(6-Chloro-9H-carbazol-2-yl)-2-trimethylsilanyloxy-propionitrile

(6-chloro-2-carbazolyl)methylmalonic acid diethyl ester

Refernces

• 1、 Liu, Xiaolong,Zhao, Meng,Fan, Xinjiong,Fu, Yao. "Reshaping the active pocket of esterase Est816 for resolution of economically important racemates". . p. 6126 - 6133. Retrieved 2021/09/28.
• 2、 Bhatthula, Bharath kumar goud,Kanchani, Janardhan reddy,Arava, Veera reddy,Subha. "Total synthesis of carbazole alkaloids". . p. 874 - 887. Retrieved 2019/01/11.