[N'-(2-benzyloxycarbonylamino-3-methyl-butyryl)-N-(3-phenethyl-oxiranecarbonyl)-hydrazino]-acetic acid tert-butyl ester

Base Information

• Chemical Name: [N'-(2-benzyloxycarbonylamino-3-methyl-butyryl)-N-(3-phenethyl-oxiranecarbonyl)-hydrazino]-acetic acid tert-butyl ester
• CAS No.: 646532-21-0
• Molecular Formula: C₃₀H₃₉N₃O₇
• Molecular Weight: 553.656

Synonyms:[N'-(2-benzyloxycarbonylamino-3-methyl-butyryl)-N-(3-phenethyl-oxiranecarbonyl)-hydrazino]-acetic acid tert-butyl ester

Chemical Property of [N'-(2-benzyloxycarbonylamino-3-methyl-butyryl)-N-(3-phenethyl-oxiranecarbonyl)-hydrazino]-acetic acid tert-butyl ester

Chemical Property:

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Technology Process of [N'-(2-benzyloxycarbonylamino-3-methyl-butyryl)-N-(3-phenethyl-oxiranecarbonyl)-hydrazino]-acetic acid tert-butyl ester

There total 7 articles about [N'-(2-benzyloxycarbonylamino-3-methyl-butyryl)-N-(3-phenethyl-oxiranecarbonyl)-hydrazino]-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: 48.0%

trans-3-phenethyloxirane-2-carboxylic acid (99773-48-5) + Cbz-Val-NHNHCH2COO-t-Bu (646532-78-7) → [N'-(2-benzyloxycarbonylamino-3-methyl-butyryl)-N-(3-phenethyl-oxiranecarbonyl)-hydrazino]-acetic acid tert-butyl ester (646532-21-0)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jm0305016

Reference yield:

3-phenyl-propionaldehyde (104-53-0) → [N'-(2-benzyloxycarbonylamino-3-methyl-butyryl)-N-(3-phenethyl-oxiranecarbonyl)-hydrazino]-acetic acid tert-butyl ester (646532-21-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / pyridine / 6 h / 100 - 105 °C

2: 61 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / tetrahydrofuran / 15.5 h / 0 - 20 °C

3: 46 percent / tert-butyl hydroperoxide; t-BuLi / toluene; tetrahydrofuran; pentane / 2 h / 20 °C

4: 72 percent / aq. NaOH / methanol / 1 h / 20 °C

5: 48 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 16 h / 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; sodium hydroxide; tert.-butyl lithium; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; pentane;

DOI:10.1021/jm0305016

Reference yield:

5-phenyl-2(E)-pentenoic acid (24271-22-5,55320-96-2,138034-94-3) → [N'-(2-benzyloxycarbonylamino-3-methyl-butyryl)-N-(3-phenethyl-oxiranecarbonyl)-hydrazino]-acetic acid tert-butyl ester (646532-21-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / tetrahydrofuran / 15.5 h / 0 - 20 °C

2: 46 percent / tert-butyl hydroperoxide; t-BuLi / toluene; tetrahydrofuran; pentane / 2 h / 20 °C

3: 72 percent / aq. NaOH / methanol / 1 h / 20 °C

4: 48 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 16 h / 20 °C

With tert.-butylhydroperoxide; dmap; sodium hydroxide; tert.-butyl lithium; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; pentane;

DOI:10.1021/jm0305016

upstream raw materials:

trans-3-phenethyloxirane-2-carboxylic acid

Cbz-Val-NHNHCH₂COO-t-Bu

3-phenyl-propionaldehyde

5-phenyl-2(E)-pentenoic acid

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