3-(2-{3-[3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionylamino}-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3-(2-{3-[3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionylamino}-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester
• CAS No.: 405927-99-3
• Molecular Formula: C₄₀H₅₇N₃O₈Si
• Molecular Weight: 735.993

Synonyms:3-(2-{3-[3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionylamino}-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester

Chemical Property of 3-(2-{3-[3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionylamino}-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester

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Technology Process of 3-(2-{3-[3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionylamino}-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester

There total 3 articles about 3-(2-{3-[3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionylamino}-2-methoxycarbonyl-ethyl)-indole-1-carboxylic 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: 84.0%

1-tert-butoxycarbonyl-L-tryptophane methyl ester (96238-70-9) + 3-[(1S,3S)-3-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionic acid → 3-(2-{3-[3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionylamino}-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester (405927-99-3)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2.5h;

DOI:10.1021/jo0160569

Reference yield:

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) → 3-(2-{3-[3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionylamino}-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester (405927-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / DMAP; EDC / 1 h / 20 °C

2: 67 percent / piperidine / dimethylformamide / 0.5 h / 20 °C

3: 84 percent / HBTU; DIEA / dimethylformamide / 2.5 h / 20 °C

With piperidine; dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jo0160569

Reference yield:

tert-butyl (S)-3-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methoxy-3-oxopropyl)-1H-indole-1-carboxylate (405555-31-9) → 3-(2-{3-[3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionylamino}-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester (405927-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / piperidine / dimethylformamide / 0.5 h / 20 °C

2: 84 percent / HBTU; DIEA / dimethylformamide / 2.5 h / 20 °C

With piperidine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jo0160569

upstream raw materials:

1-tert-butoxycarbonyl-L-tryptophane methyl ester

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester

tert-butyl (S)-3-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methoxy-3-oxopropyl)-1H-indole-1-carboxylate

Downstream raw materials:

C₆₇H₉₆N₆O₁₃Si

C₆₁H₈₀N₆O₁₃

C₆₁H₈₂N₆O₁₃

3-(2-{3-[3-[(2-benzyloxycarbonylamino-3-phenyl-propionyl)-(6-tert-butoxycarbonylamino-hexyl)-amino]-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-propionylamino}-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester

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