(S)-2-[(S)-4-tert-Butoxycarbonyl-4-((S)-4-tert-butoxycarbonyl-4-{4-[(4-chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid di-tert-butyl ester

Base Information

• Chemical Name: (S)-2-[(S)-4-tert-Butoxycarbonyl-4-((S)-4-tert-butoxycarbonyl-4-{4-[(4-chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid di-tert-butyl ester
• CAS No.: 138899-83-9
• Molecular Formula: C₅₂H₆₉ClFN₅O₁₁
• Molecular Weight: 994.598

Synonyms:(S)-2-[(S)-4-tert-Butoxycarbonyl-4-((S)-4-tert-butoxycarbonyl-4-{4-[(4-chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid di-tert-butyl ester

Chemical Property of (S)-2-[(S)-4-tert-Butoxycarbonyl-4-((S)-4-tert-butoxycarbonyl-4-{4-[(4-chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid di-tert-butyl ester

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Technology Process of (S)-2-[(S)-4-tert-Butoxycarbonyl-4-((S)-4-tert-butoxycarbonyl-4-{4-[(4-chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid di-tert-butyl ester

There total 3 articles about (S)-2-[(S)-4-tert-Butoxycarbonyl-4-((S)-4-tert-butoxycarbonyl-4-{4-[(4-chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid di-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: 60.0%

L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-glutamic acid pentakis-t-butyl ester (88443-03-2) + 4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoic acid (138899-81-7) → (S)-2-[(S)-4-tert-Butoxycarbonyl-4-((S)-4-tert-butoxycarbonyl-4-{4-[(4-chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid di-tert-butyl ester (138899-83-9)

Guidance literature:

With diethyl cyanophosphoridate; triethylamine; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1021/jm00083a008

Reference yield:

penta-tert-butyl N--L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate (32816-47-0) → (S)-2-[(S)-4-tert-Butoxycarbonyl-4-((S)-4-tert-butoxycarbonyl-4-{4-[(4-chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid di-tert-butyl ester (138899-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / ethyl acetate / 2.5 h / 760 Torr

2: 60 percent / diethyl cyanophosphoridate, Et₃N / dimethylformamide / 2 h / Ambient temperature

With diethyl cyanophosphoridate; hydrogen; triethylamine; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00083a008

Reference yield:

N-[4-[N-(4-chloro-2-methylquinolin-6-ylmethyl)-N-(prop-2-ynyl)amino]-2-fluorobenzoyl]-L-glutamic acid (123636-66-8) → (S)-2-[(S)-4-tert-Butoxycarbonyl-4-((S)-4-tert-butoxycarbonyl-4-{4-[(4-chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid di-tert-butyl ester (138899-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Tris buffer (tris(hydroxymethyl)aminomethane, ZnCl₂, aq. HCl, pH 7.3) / 1.5 h / 37 °C / carboxypeptidase G₂

2: 60 percent / diethyl cyanophosphoridate, Et₃N / dimethylformamide / 2 h / Ambient temperature

With diethyl cyanophosphoridate; Tris buffer (tris(hydroxymethyl)aminomethane, ZnCl₂, aq. HCl, pH 7.3); triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jm00083a008

upstream raw materials:

L-γ-glutamyl-L-γ-glutamyl-L-γ-glutamyl-L-glutamic acid pentakis-t-butyl ester

4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoic acid

penta-tert-butyl N--L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate

N-[4-[N-(4-chloro-2-methylquinolin-6-ylmethyl)-N-(prop-2-ynyl)amino]-2-fluorobenzoyl]-L-glutamic acid

Downstream raw materials:

(S)-2-[(S)-4-Carboxy-4-((S)-4-carboxy-4-{4-[(4-chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-2-fluoro-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid; compound with trifluoro-acetic acid

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