[(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

Base Information

• Chemical Name: [(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
• CAS No.: 628729-11-3
• Molecular Formula: C₃₁H₄₈N₄O₆
• Molecular Weight: 572.745
• Mol file: 628729-11-3.mol

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 10 articles about [(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 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: 63.0%

3-Amino-2-hydroxy-hexanoic acid ((S)-1-phenyl-ethyl)-amide + (1S,3aR,6aS)-2-((S)-2-Isopropoxycarbonylamino-3-methyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid (628729-07-7) → [(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 (628729-11-3)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In tetrahydrofuran;

DOI:10.1016/S0960-894X(03)00753-4

Reference yield:

L-valine benzyl ester hydrochloride (2462-34-2) → [(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 (628729-11-3)

Guidance literature:

Multi-step reaction with 5 steps

1: i-Pr₂EtN

2: 100 percent / H₂ / Pd/C

3: 73 percent / HOAt; EDCI / tetrahydrofuran

4: 85 percent / aq. NaOH / ethanol

5: 63 percent / PyBOP / tetrahydrofuran

With sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1016/S0960-894X(03)00753-4

Reference yield:

(S)-2-Isopropoxycarbonylamino-3-methyl-butyric acid benzyl ester (628729-15-7) → [(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 (628729-11-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / H₂ / Pd/C

2: 73 percent / HOAt; EDCI / tetrahydrofuran

3: 85 percent / aq. NaOH / ethanol

4: 63 percent / PyBOP / tetrahydrofuran

With sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1016/S0960-894X(03)00753-4

upstream raw materials:

(1S,3aR,6aS)-2-((S)-2-Isopropoxycarbonylamino-3-methyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid

N-isopropoxycarbonyl-S-valine

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

(1S,3aR,6aS)-2-((S)-2-Isopropoxycarbonylamino-3-methyl-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid ethyl ester

Refernces

• 1、 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.