tetra-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate

Base Information

• Chemical Name: tetra-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate
• CAS No.: 117559-49-6
• Molecular Formula: C₅₀H₆₉N₇O₁₂
• Molecular Weight: 960.138

Synonyms:tetra-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate

Chemical Property of tetra-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate

Chemical Property:

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Technology Process of tetra-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate

There total 9 articles about tetra-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate 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%

2-amino-6-(bromomethyl)-4-hydroxyquinazoline hydrobromide (77766-62-2) + tetra-tert-butyl N--L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate (117559-45-2) → tetra-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate (117559-49-6)

Guidance literature:

With calcium carbonate; In N,N-dimethyl acetamide; for 420h; Ambient temperature;

DOI:10.1021/jm00121a029

Reference yield:

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester (5891-45-2) → tetra-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate (117559-49-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) N-methylmorpholine, isobutylchloroformate / 1) THF, -20 deg C, 10 min, 2) THF, -20 deg C, 10 min

2: H₂ / 10percent Pd/C / methanol

3: 1) N-methylmorpholine, isobutylchloroformate / 1) THF, -20 deg C, 10 min, 2) THF, -20 deg C, 10 min

4: H₂ / 10percent Pd/C / methanol

5: 86 percent / N-methylmorpholine / dioxane / 0.33 h / Ambient temperature

6: H₂ / 10percent Pd/C / methanol / 1 h

7: 64 percent / 2,6-dimethylpyridine / dimethylformamide / 120 h / Ambient temperature

8: 72 percent / CaCO₃ / N,N-dimethyl-acetamide / 420 h / Ambient temperature

With 4-methyl-morpholine; 2,6-dimethylpyridine; hydrogen; calcium carbonate; isobutyl chloroformate; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1021/jm00121a029

Reference yield:

L-glutamic acid di-tert-butyl ester hydrochloride (32677-01-3) → tetra-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate (117559-49-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) N-methylmorpholine, isobutylchloroformate / 1) THF, -20 deg C, 10 min, 2) THF, -20 deg C, 10 min

2: H₂ / 10percent Pd/C / methanol

3: 1) N-methylmorpholine, isobutylchloroformate / 1) THF, -20 deg C, 10 min, 2) THF, -20 deg C, 10 min

4: H₂ / 10percent Pd/C / methanol

5: 86 percent / N-methylmorpholine / dioxane / 0.33 h / Ambient temperature

6: H₂ / 10percent Pd/C / methanol / 1 h

7: 64 percent / 2,6-dimethylpyridine / dimethylformamide / 120 h / Ambient temperature

8: 72 percent / CaCO₃ / N,N-dimethyl-acetamide / 420 h / Ambient temperature

With 4-methyl-morpholine; 2,6-dimethylpyridine; hydrogen; calcium carbonate; isobutyl chloroformate; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1021/jm00121a029

upstream raw materials:

2-amino-6-(bromomethyl)-4-hydroxyquinazoline hydrobromide

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

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester

L-glutamic acid di-tert-butyl ester hydrochloride

Downstream raw materials:

N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamic acid trifluoroacetate salt

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