N^α-[3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbamoyl)propionyl]-leucyl-O-methyl-tyrosine N-methylamide

Base Information

• Chemical Name: N^α-[3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbamoyl)propionyl]-leucyl-O-methyl-tyrosine N-methylamide
• CAS No.: 458532-03-1
• Molecular Formula: C₃₃H₄₇N₅O₈
• Molecular Weight: 641.765

Synonyms:N^α-[3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbamoyl)propionyl]-leucyl-O-methyl-tyrosine N-methylamide

Chemical Property of N^α-[3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbamoyl)propionyl]-leucyl-O-methyl-tyrosine N-methylamide

Chemical Property:

Purity/Quality:

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Technology Process of N^α-[3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbamoyl)propionyl]-leucyl-O-methyl-tyrosine N-methylamide

There total 5 articles about N^α-[3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbamoyl)propionyl]-leucyl-O-methyl-tyrosine N-methylamide 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: 90.0%

O-benzylhydoxylamine hydrochloride (2687-43-6) + 2-(tert-butoxycarbonylamino-methyl)-N-{1-[2-(4-methoxy-phenyl)-1-methylcarbamoyl-ethylcarbamoyl]-3-methyl-butyl}-malonamic acid (458532-02-0) → Nα-[3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbamoyl)propionyl]-leucyl-O-methyl-tyrosine N-methylamide (458532-03-1)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at -3 - 0 ℃; for 21h;

DOI:10.1248/cpb.50.239

Reference yield:

benzyl 3-(tert-butyloxycarbonylamino)propionate (88574-54-3) → Nα-[3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbamoyl)propionyl]-leucyl-O-methyl-tyrosine N-methylamide (458532-03-1)

Guidance literature:

Multi-step reaction with 4 steps

1: LDA / tetrahydrofuran; hexane / 0.33 h / -70 °C

2: EDC; Et₃N; HOBt / dimethylformamide / 21 h / -3 - 0 °C

3: 91 percent / H₂ / 10 percent Pd/C / methanol / 1 h / 20 °C / normal pressure

4: 90 percent / EDC; Et₃N; HOBt / dimethylformamide / 21 h / -3 - 0 °C

With hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.50.239

Reference yield:

3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbonyl)propionic acid → Nα-[3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbamoyl)propionyl]-leucyl-O-methyl-tyrosine N-methylamide (458532-03-1)

Guidance literature:

Multi-step reaction with 3 steps

1: EDC; Et₃N; HOBt / dimethylformamide / 21 h / -3 - 0 °C

2: 91 percent / H₂ / 10 percent Pd/C / methanol / 1 h / 20 °C / normal pressure

3: 90 percent / EDC; Et₃N; HOBt / dimethylformamide / 21 h / -3 - 0 °C

With hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.50.239

upstream raw materials:

O-benzylhydoxylamine hydrochloride

2-(tert-butoxycarbonylamino-methyl)-N-{1-[2-(4-methoxy-phenyl)-1-methylcarbamoyl-ethylcarbamoyl]-3-methyl-butyl}-malonamic acid

benzyl 3-(tert-butyloxycarbonylamino)propionate

N^α-[3-(tert-butyloxycarbonylamino)-2(R,S)-(benzyloxycarbonyl)propionyl]-leucyl-O-methyl-tyrosine N-methylamide

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