Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-4-hydroxy-, 1-ethyl 2-(phenylmethyl) ester, (1S,3aR,6aS)-

Base Information

• Chemical Name: Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-4-hydroxy-, 1-ethyl 2-(phenylmethyl) ester, (1S,3aR,6aS)-
• CAS No.: 402958-22-9
• Molecular Formula: C18H23NO5
• Molecular Weight: 333.384
• Mol file: 402958-22-9.mol

Synonyms:

Chemical Property of Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-4-hydroxy-, 1-ethyl 2-(phenylmethyl) ester, (1S,3aR,6aS)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-4-hydroxy-, 1-ethyl 2-(phenylmethyl) ester, (1S,3aR,6aS)-

There total 1 articles about Cyclopenta[c]pyrrole-1,2(1H)-dicarboxylic acid, hexahydro-4-hydroxy-, 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: 92.0%

(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)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (402958-22-9)

Guidance literature:

(1S,3aR,6aS)-4-Oxo-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester; With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.5h;

With acetic acid; In ethanol;

With sodium hydrogencarbonate; In ethanol; water; ethyl acetate;

Reference yield:

(1S,3aR,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (402958-22-9) → (S)-2-(3-{[(1S,3aR,6aS)-2-((S)-3-Methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-4-oxo-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-2-oxo-hexanoylamino)-3-phenyl-propionic acid

Guidance literature:

Multi-step reaction with 6 steps

1.1: H₂ / Pd(OH)2/C / ethanol

2.1: HOAt; DCC

2.2: i-Pr₂EtN

3.1: aq. NaOH / ethanol

4.1: PyBOP

4.2: 68 percent / i-Pr₂EtN

5.1: Dess-Martin periodinane / tetrahydrofuran

6.1: TFA / CH₂Cl₂

With sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; Dess-Martin periodane; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; 5.1: Dess-Martin oxidation;

DOI:10.1016/j.bmcl.2003.09.074

Reference yield:

(1S,3aR,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (402958-22-9) → (S)-2-(3-{[(1S,3aR,6aS)-2-((S)-3-Methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-4-oxo-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-2-oxo-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / Pd(OH)2/C / ethanol

2.1: HOAt; DCC

2.2: i-Pr₂EtN

3.1: aq. NaOH / ethanol

4.1: PyBOP

4.2: 68 percent / i-Pr₂EtN

5.1: Dess-Martin periodinane / tetrahydrofuran

With sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; Dess-Martin periodane; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; ethanol; 5.1: Dess-Martin oxidation;

DOI:10.1016/j.bmcl.2003.09.074

upstream raw materials:

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

Downstream raw materials:

(1S,3aR,6aS)-4-Hydroxy-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid ethyl ester

(S)-2-(2-Hydroxy-3-{[(1S,3aR,6aS)-4-hydroxy-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

(1S,3aR,6aS)-ethyl octahydrocyclopenta[c]pyrrole-1-carboxylate

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

Refernces

• 1、 -. "3,4-(cyclopentyl)-fused proline compounds as inhibitors of hepatitis C virus NS3 serine protease". Page/Page column 118-119. . Retrieved 2008/06/13.