(S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-((S)-4-carboxy-4-{4-[(4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid; compound with trifluoro-acetic acid

Base Information

• Chemical Name: (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-((S)-4-carboxy-4-{4-[(4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid; compound with trifluoro-acetic acid
• CAS No.: 138899-66-8
• Molecular Formula: C₂HF₃O₂*2C₃₉H₄₃N₇O₁₅
• Molecular Weight: 1813.64

Synonyms:(S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-((S)-4-carboxy-4-{4-[(4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid; compound with trifluoro-acetic acid

Chemical Property of (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-((S)-4-carboxy-4-{4-[(4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid; compound with trifluoro-acetic acid

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Technology Process of (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-((S)-4-carboxy-4-{4-[(4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid; compound with trifluoro-acetic acid

There total 5 articles about (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-((S)-4-carboxy-4-{4-[(4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid; compound with trifluoro-acetic acid 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: 93.0%

C59H83N7O15 (138899-68-0) + trifluoroacetic acid (76-05-1) → (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-((S)-4-carboxy-4-{4-[(4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid; compound with trifluoro-acetic acid (138899-66-8)

Guidance literature:

for 1h; 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-Carboxy-4-[(S)-4-carboxy-4-((S)-4-carboxy-4-{4-[(4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid; compound with trifluoro-acetic acid (138899-66-8)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 54 percent / diethyl cyanophosphoridate, Et₃N / dimethylformamide / 2 h / Ambient temperature

3: 93 percent / 1 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-[(3,4-dihydro-4-oxo-6-quinazolinyl)methyl]-prop-2-ynylamino}benzoyl)-L-glutamic acid (106585-65-3) → (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-((S)-4-carboxy-4-{4-[(4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid; compound with trifluoro-acetic acid (138899-66-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / Tris buffer (tris(hydroxymethyl)aminomethane, ZnCl₂, aq. HCl, pH 7.3) / 1.5 h / 37 °C / carboxypeptidase G₂

2: 54 percent / diethyl cyanophosphoridate, Et₃N / dimethylformamide / 2 h / Ambient temperature

3: 93 percent / 1 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:

C₅₉H₈₃N₇O₁₅

trifluoroacetic acid

N-(4-{N-[(3,4-dihydro-4-oxo-6-quinazolinyl)methyl]-prop-2-ynylamino}benzoyl)-L-glutamic acid

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

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