Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-, 1-ethyl 2-(phenylmethyl) ester, (1S,3aR,6aS)-

Base Information

• Chemical Name: Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-, 1-ethyl 2-(phenylmethyl) ester, (1S,3aR,6aS)-
• CAS No.: 402958-24-1
• Molecular Formula: C18H23NO4
• Molecular Weight: 317.385
• Mol file: 402958-24-1.mol

Synonyms:Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid,hexahydro-,1-ethyl-2-(phenylmethyl) ester,(1R,3aS,6aR);CYC022;

Chemical Property of Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-, 1-ethyl 2-(phenylmethyl) ester, (1S,3aR,6aS)-

Chemical Property:

• PSA: 55.84000
• LogP: 2.92470

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-, 1-ethyl 2-(phenylmethyl) ester, (1S,3aR,6aS)-

There total 10 articles about Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-, 1-ethyl 2-(phenylmethyl) ester, (1S,3aR,6aS)- 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: 98.0%

(1S,3aR,6aS)-4-Methylsulfanylthiocarboxyoxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (402958-23-0) → (1S,3aR,6aS)-Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (402958-24-1,864185-80-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 95 ℃; for 1h;

Reference yield:

C24H29N3O6S → (1S,3aR,6aS)-Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (402958-24-1,864185-80-8)

Guidance literature:

With sodium ethanolate; In ethanol; for 5h; Reflux;

Reference yield:

(1S,3aR,6aS)-4-Oxo-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (402958-21-8,158340-62-6) → (1S,3aR,6aS)-Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (402958-24-1,864185-80-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / ethanol

2: NaH / tetrahydrofuran

3: n-Bu₃SnH; AIBN / toluene

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; ethanol; toluene; 3: Barton deoxygenation;

DOI:10.1016/j.bmcl.2003.09.074

upstream raw materials:

(1S,3aR,6aS)-4-Methylsulfanylthiocarboxyoxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

(1S,3aR,6aS)-4-Oxo-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

(1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

(1S,3aR,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Downstream raw materials:

(S)-2-(2-Hydroxy-3-{[(1S,3aR,6aS)-2-((S)-3-methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester

(S)-2-(3-{[(1S,3aR,6aS)-2-((S)-3-Methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-2-oxo-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester

[(S)-1-((1S,3aR,6aS)-1-{1-[Hydroxy-((S)-1-phenyl-ethylcarbamoyl)-methyl]-butylcarbamoyl}-hexahydro-cyclopenta[c]pyrrole-2-carbonyl)-2-methyl-propyl]-carbamic acid isopropyl ester

[(S)-1-((1S,3aR,6aS)-1-{1-[Hydroxy-((S)-1-phenyl-ethylcarbamoyl)-methyl]-butylcarbamoyl}-hexahydro-cyclopenta[c]pyrrole-2-carbonyl)-2,2-dimethyl-propyl]-carbamic acid isopropyl ester

Refernces

• 1、 -. "3,4-(cyclopentyl)-fused proline compounds as inhibitors of hepatitis C virus NS3 serine protease". Page/Page column 119. . Retrieved 2008/06/13.
• 2、 Chen, Shu-Hui,Lamar, Jason,Victor, Frantz,Snyder, Nancy,Johnson, Robert,Heinz, Beverly A.,Wakulchik, Mark,Wang, Q. May. "Synthesis and evaluation of tripeptidyl α-ketoamides as human rhinovirus 3C protease inhibitors". . p. 3531 - 3536. Retrieved 2007/10/03.