methyl (S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidine-3-carboxylate

Base Information

• Chemical Name: methyl (S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidine-3-carboxylate
• CAS No.: 442682-29-3
• Molecular Formula: C₃₇H₄₅N₅O₇S
• Molecular Weight: 703.86
• Mol file: 442682-29-3.mol

Synonyms:methyl (S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidine-3-carboxylate

Chemical Property of methyl (S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidine-3-carboxylate

There total 3 articles about methyl (S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidine-3-carboxylate 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: 97.0%

L-phenylalanine-L-proline methyl ester (83825-04-1,126251-10-3) + 2-[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid (442682-28-2) → methyl (S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidine-3-carboxylate (442682-29-3)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1246/bcsj.75.847

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → methyl (S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidine-3-carboxylate (442682-29-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / [benzotriazol-1-yloxy-tris(dimethylamino)phosphonium]PF₆; triethylamine / dimethylformamide / 0 - 20 °C

2: 100 percent / NaOH / H₂O; methanol / 2 h / 0 °C

3: 97 percent / [benzotriazol-1-yloxy-tris(dimethylamino)phosphonium]PF₆; triethylamine / dimethylformamide / 0 - 20 °C

With sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.75.847

Reference yield:

methyl 2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}-thiazole-4-carboxylate (347191-35-9) → methyl (S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidine-3-carboxylate (442682-29-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaOH / H₂O; methanol / 2 h / 0 °C

2: 97 percent / [benzotriazol-1-yloxy-tris(dimethylamino)phosphonium]PF₆; triethylamine / dimethylformamide / 0 - 20 °C

With sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.75.847

upstream raw materials:

L-phenylalanine-L-proline methyl ester

2-[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid

N-tert-butoxycarbonyl-L-phenylalanine

methyl 2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}-thiazole-4-carboxylate

Downstream raw materials:

methyl (2S,3S)-2-[(2S,3S)-{(S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidin-2-ylcarbonylamino}-3-methylpentanoylamino]-3-hydroxybutanoate

C₄₁H₄₉N₇O₆S

cis,cis-Ceratospongamide

(S)-1-[(S)-2-({2-[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carbonyl}-amino)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid