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

Base Information

• Chemical Name: penta-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate
• CAS No.: 117559-50-9
• Molecular Formula: C₅₉H₈₄N₈O₁₅
• Molecular Weight: 1145.36
• Mol file: 117559-50-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about penta-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-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: 52.0%

2-amino-6-(bromomethyl)-4-hydroxyquinazoline hydrobromide (77766-62-2) + penta-tert-butyl N--L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate (117559-46-3) → penta-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate (117559-50-9)

Guidance literature:

With calcium carbonate; In N,N-dimethyl acetamide; for 60h; Ambient temperature;

DOI:10.1021/jm00121a029

Reference yield:

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester (5891-45-2) → penta-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate (117559-50-9)

Guidance literature:

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

6: H₂ / 10percent Pd/C / methanol

7: 88 percent / N-methylmorpholine / dioxane / 0.33 h / Ambient temperature

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

9: 39 percent / CaCO₃ / N,N-dimethyl-acetamide / 60 h / Ambient temperature

10: 52 percent / CaCO₃ / N,N-dimethyl-acetamide / 60 h / Ambient temperature

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

DOI:10.1021/jm00121a029

Reference yield:

L-glutamic acid di-tert-butyl ester hydrochloride (32677-01-3) → penta-tert-butyl N-prop-2-ynylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate (117559-50-9)

Guidance literature:

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

6: H₂ / 10percent Pd/C / methanol

7: 88 percent / N-methylmorpholine / dioxane / 0.33 h / Ambient temperature

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

9: 39 percent / CaCO₃ / N,N-dimethyl-acetamide / 60 h / Ambient temperature

10: 52 percent / CaCO₃ / N,N-dimethyl-acetamide / 60 h / Ambient temperature

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

DOI:10.1021/jm00121a029

upstream raw materials:

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

penta-tert-butyl N--L-γ-glutamyl>-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-γ-glutamyl>-L-glutamic acid trifluoroacetate salt

Refernces