[(2-{2-[5-benzyloxycarbonylamino-1-(oxazole-2-carbonyl)-pentylcarbamoyl]-pyrrolidin-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-tert-butoxycarbonyl-amino]-acetic acid tert-butyl ester

Base Information

• Chemical Name: [(2-{2-[5-benzyloxycarbonylamino-1-(oxazole-2-carbonyl)-pentylcarbamoyl]-pyrrolidin-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-tert-butoxycarbonyl-amino]-acetic acid tert-butyl ester
• CAS No.: 190904-94-0
• Molecular Formula: C₄₂H₆₁N₅O₁₀
• Molecular Weight: 795.974
• Mol file: 190904-94-0.mol

Synonyms:[(2-{2-[5-benzyloxycarbonylamino-1-(oxazole-2-carbonyl)-pentylcarbamoyl]-pyrrolidin-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-tert-butoxycarbonyl-amino]-acetic acid tert-butyl ester

Chemical Property of [(2-{2-[5-benzyloxycarbonylamino-1-(oxazole-2-carbonyl)-pentylcarbamoyl]-pyrrolidin-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-tert-butoxycarbonyl-amino]-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2-{2-[5-benzyloxycarbonylamino-1-(oxazole-2-carbonyl)-pentylcarbamoyl]-pyrrolidin-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-tert-butoxycarbonyl-amino]-acetic acid tert-butyl ester

There total 9 articles about [(2-{2-[5-benzyloxycarbonylamino-1-(oxazole-2-carbonyl)-pentylcarbamoyl]-pyrrolidin-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-tert-butoxycarbonyl-amino]-acetic acid tert-butyl 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:

di-tert-butyl dicarbonate (24424-99-5) → [(2-{2-[5-benzyloxycarbonylamino-1-(oxazole-2-carbonyl)-pentylcarbamoyl]-pyrrolidin-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-tert-butoxycarbonyl-amino]-acetic acid tert-butyl ester (190904-94-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / DiPEA / dimethylformamide / 16 h / 20 °C / pH 8.5

2: 93 percent / aq. NaOH / dioxane / 6 h / 20 °C / pH 12

3: 75 percent / HOBt; DCCI; Et₃N / dimethylformamide / 0 - 20 °C

4: 89 percent / H₂ / 10percent Pd/C / methanol / 1 h / 20 °C / atmospheric pressure

5: HOBt; DCCI; Et₃N / dimethylformamide / 0 - 20 °C / pH 8.5

With sodium hydroxide; hydrogen; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 10percent Pd/C; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm011110z

Reference yield:

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) → [(2-{2-[5-benzyloxycarbonylamino-1-(oxazole-2-carbonyl)-pentylcarbamoyl]-pyrrolidin-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-tert-butoxycarbonyl-amino]-acetic acid tert-butyl ester (190904-94-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / HOBt; DCCI; Et₃N / dimethylformamide / 0 - 20 °C

2: 89 percent / H₂ / 10percent Pd/C / methanol / 1 h / 20 °C / atmospheric pressure

3: HOBt; DCCI; Et₃N / dimethylformamide / 0 - 20 °C / pH 8.5

With hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; 10percent Pd/C; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm011110z

Reference yield:

D-cyclohexylalanine hydrochloride (151899-07-9) → [(2-{2-[5-benzyloxycarbonylamino-1-(oxazole-2-carbonyl)-pentylcarbamoyl]-pyrrolidin-1-yl}-1-cyclohexylmethyl-2-oxo-ethyl)-tert-butoxycarbonyl-amino]-acetic acid tert-butyl ester (190904-94-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / thionyl chloride / 5 h / Heating

2: DiPEA / acetonitrile / 16 h / 20 °C / pH 8.5

3: 70 percent / DiPEA / dimethylformamide / 16 h / 20 °C / pH 8.5

4: 93 percent / aq. NaOH / dioxane / 6 h / 20 °C / pH 12

5: 75 percent / HOBt; DCCI; Et₃N / dimethylformamide / 0 - 20 °C

6: 89 percent / H₂ / 10percent Pd/C / methanol / 1 h / 20 °C / atmospheric pressure

7: HOBt; DCCI; Et₃N / dimethylformamide / 0 - 20 °C / pH 8.5

With sodium hydroxide; thionyl chloride; hydrogen; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 10percent Pd/C; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm011110z

upstream raw materials:

(2S)-1-((2R)-2-{(tert-butoxycarbonyl)[2-(tert-butoxy)-2-oxoethyl]amino}-3-cyclohexylpropanoyl)-L-proline

di-tert-butyl dicarbonate

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

D-cyclohexylalanine hydrochloride