(2Z)-2-[1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid

Base Information

• Chemical Name: (2Z)-2-[1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid
• CAS No.: 204204-73-9
• Molecular Formula: C₁₈H₂₀FNO₃S
• Molecular Weight: 349.426
• DSSTox Substance ID: DTXSID50439427
• Nikkaji Number: J1.310.310K,J1.761.878D
• Wikidata: Q27088504
• ChEMBL ID: CHEMBL3526431
• Mol file: 204204-73-9.mol

Synonyms:R-138727

Chemical Property of (2Z)-2-[1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid

Chemical Property:

• PSA: 96.41000
• LogP: 2.79890
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 349.11479284
• Heavy Atom Count: 24
• Complexity: 534

Purity/Quality:

99%min ^*data from raw suppliers

PRASUGREL-D4-METABOLITE-R-138727 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C(=O)C(C2=CC=CC=C2F)N3CCC(C(=CC(=O)O)C3)S
• Isomeric SMILES: C1CC1C(=O)C(C2=CC=CC=C2F)N3CCC(/C(=C\C(=O)O)/C3)S
• Uses: The active metabolite of Prasugrel (P701150); inhibits ADP-stimulated thrombo-inflammatory markers of platelet activation: influence of other blood cells, calcium, and aspirin.

Technology Process of (2Z)-2-[1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid

There total 15 articles about (2Z)-2-[1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic 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: 90.12%

C19H22FNO3S → R-138727 (204204-98-8,204204-73-9)

Guidance literature:

With sodium hydroxide;

Reference yield: 7.8%

→ R-138727 (204204-73-9)

Guidance literature:

Reference yield:

5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine → R-138727 (204204-98-8,204204-73-9)

Guidance literature:

5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine; With calcium chloride; cytochrome P₄₅₀; pH=7.4; aq. phosphate buffer;

With GLUTATHIONE; at 37 ℃; for 0.5h; pH=7.4; aq. phosphate buffer;

DOI:10.1021/tx3000279

upstream raw materials:

C₁₈H₂₀FNO₄S

prasugel

5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

GLUTATHIONE

Downstream raw materials:

C₂₇H₂₈FNO₅S

Refernces

• 1、 Dansette, Patrick M.,Levent, Dan,Hessani, Assia,Mansuy, Daniel. "Bioactivation of Clopidogrel and Prasugrel: Factors Determining the Stereochemistry of the Thiol Metabolite Double Bond". . p. 1338 - 1345. Retrieved 2015/06/25.
• 2、 Hagihara, Katsunobu,Kazui, Miho,Kurihara, Atsushi,Iwabuchi, Haruo,Ishikawa, Minoru,Kobayashi, Hiroyuki,Tanaka, Naoki,Okazaki, Osamu,Farid, Nagy A.,Ikeda, Toshihiko. "Biotransformation of prasugrel, a novel thienopyridine antiplatelet agent, to the pharmacologically active metabolite". . p. 898 - 904. Retrieved 2011/03/18.