(S)-3-{(S)-6-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester

Base Information

• Chemical Name: (S)-3-{(S)-6-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester
• CAS No.: 131450-41-4
• Molecular Formula: C₅₀H₅₉N₇O₁₀
• Molecular Weight: 918.059

Synonyms:(S)-3-{(S)-6-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester

Chemical Property of (S)-3-{(S)-6-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester

Chemical Property:

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Technology Process of (S)-3-{(S)-6-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester

There total 7 articles about (S)-3-{(S)-6-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl 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:

2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-tryptophanate (3392-11-8) + H-Lys(CBz)-Asp(OBn)-Phe-NH2 hydrochloride (131450-40-3) → (S)-3-{(S)-6-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester (131450-41-4)

Guidance literature:

With 4-methyl-morpholine; In N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1021/jm00113a023

Reference yield:

Boc-Lys(Z)-OH (2389-45-9) → (S)-3-{(S)-6-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester (131450-41-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / N-methylmorpholine, HOBt, EDCI / dimethylformamide; CH₂Cl₂ / 12 h / Ambient temperature

2: aq. HCl / acetic acid / 1.5 h / Ambient temperature

3: 11.9 g / N-methylmorpholine / dimethylformamide / 18 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a023

Reference yield:

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → (S)-3-{(S)-6-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester (131450-41-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / N-methylmorpholine, HOBt, EDCI / dimethylformamide; CH₂Cl₂ / 12 h / Ambient temperature

2: aq. HCl / acetic acid / 1.5 h / Ambient temperature

3: 90 percent / N-methylmorpholine, HOBt, EDCI / dimethylformamide; CH₂Cl₂ / 12 h / Ambient temperature

4: aq. HCl / acetic acid / 1.5 h / Ambient temperature

5: 11.9 g / N-methylmorpholine / dimethylformamide / 18 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a023

upstream raw materials:

2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-tryptophanate

H-Lys(CBz)-Asp(OBn)-Phe-NH₂ hydrochloride

Boc-Lys(Z)-OH

BOC-L-aspartic acid 4-benzyl ester

Downstream raw materials:

Boc-Trp-Lys-Asp-Phe-NH₂

Boc-Trp-Lys-Asp-Phe-NH₂ acetic acid salt

(S)-3-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-6-[3-(2-nitro-phenyl)-ureido]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid

(S)-3-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-6-[3-(2-methoxy-phenyl)-ureido]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid

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