N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide

Base Information

• Chemical Name: N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide
• CAS No.: 280781-54-6
• Molecular Formula: C₃₂H₃₆N₄O₄S
• Molecular Weight: 572.728
• Mol file: 280781-54-6.mol

Synonyms:N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide

Chemical Property of N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide

There total 12 articles about N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide 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: 72.0%

bromoacetic acid tert-butyl ester (5292-43-3) + D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide (785764-66-1) → N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide (280781-54-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 48h;

DOI:10.1021/jm030025j

Reference yield:

5-(bromomethyl)thiophene-2-carbonitrile (134135-41-4) → N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide (280781-54-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / tetrahydrofuran / 3 h

2: 2.4 g / HCl(g) / ethyl acetate / 0 - 20 °C

3: 86 percent / EDC; HOBT; Et₃N / dimethylformamide / 20 °C

4: 100 percent / HCl / ethyl acetate / 3 h / 20 °C

5: 72 percent / iPr₂NEt / acetonitrile / 48 h / 20 °C

With hydrogenchloride; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm030025j

Reference yield:

N-Boc-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide (280781-39-7) → N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide (280781-54-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / HCl / ethyl acetate / 3 h / 20 °C

2: 72 percent / iPr₂NEt / acetonitrile / 48 h / 20 °C

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; In ethyl acetate; acetonitrile;

DOI:10.1021/jm030025j

upstream raw materials:

bromoacetic acid tert-butyl ester

D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide

2-bromo-5-methyl thiophene

2-cyano-5-methylthiophene

Downstream raw materials:

N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl[(5-hydroxyamidino-2-thienyl)methyl]amide

2-{[(1R)-2-((2S)-2{[({5-[amino(imino)methyl]-2-thienyl}methyl)amino]carbonyl}-pyrrolidinyl)-1-benzhydryl-2-oxoethyl]amino}acetic acid