trans-3-(N²-(N-3-phenylpropanoylvalylalanyl)-N¹-tert-butoxycarbonylmethylhydrazinocarbonyl)-2-(2-phenethyl)oxirane

Base Information

• Chemical Name: trans-3-(N²-(N-3-phenylpropanoylvalylalanyl)-N¹-tert-butoxycarbonylmethylhydrazinocarbonyl)-2-(2-phenethyl)oxirane
• CAS No.: 646531-06-8
• Molecular Formula: C₃₄H₄₆N₄O₇
• Molecular Weight: 622.762
• Mol file: 646531-06-8.mol

Synonyms:trans-3-(N²-(N-3-phenylpropanoylvalylalanyl)-N¹-tert-butoxycarbonylmethylhydrazinocarbonyl)-2-(2-phenethyl)oxirane

Chemical Property of trans-3-(N²-(N-3-phenylpropanoylvalylalanyl)-N¹-tert-butoxycarbonylmethylhydrazinocarbonyl)-2-(2-phenethyl)oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-3-(N²-(N-3-phenylpropanoylvalylalanyl)-N¹-tert-butoxycarbonylmethylhydrazinocarbonyl)-2-(2-phenethyl)oxirane

There total 16 articles about trans-3-(N²-(N-3-phenylpropanoylvalylalanyl)-N¹-tert-butoxycarbonylmethylhydrazinocarbonyl)-2-(2-phenethyl)oxirane 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: 38.0%

trans-3-phenethyloxirane-2-carboxylic acid (99773-48-5) + 3-phenylpropanoyl-Val-Ala-NHNHCH2COO-t-Bu (646532-77-6) → trans-3-(N2-(N-3-phenylpropanoylvalylalanyl)-N1-tert-butoxycarbonylmethylhydrazinocarbonyl)-2-(2-phenethyl)oxirane (646531-06-8)

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: 38.0%

trans-3-phenethyloxirane-2-carboxylic acid (99773-48-5) + 3-phenylpropanoyl-Val-Ala-NHNHCH2COO-t-Bu (646532-77-6) → trans-3-(N2-(N-3-phenylpropanoylvalylalanyl)-N1-t-butoxycarbonylmethylhydrazinocarbonyl)-2-(2-phenylethyl)oxirane (646531-06-8)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jm025581c

Reference yield:

3-phenyl-propionaldehyde (104-53-0) → trans-3-(N2-(N-3-phenylpropanoylvalylalanyl)-N1-tert-butoxycarbonylmethylhydrazinocarbonyl)-2-(2-phenethyl)oxirane (646531-06-8)

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: 38 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

upstream raw materials:

trans-3-phenethyloxirane-2-carboxylic acid

3-phenylpropanoyl-Val-Ala-NHNHCH₂COO-t-Bu

3-phenyl-propionaldehyde

bromoacetic acid tert-butyl ester