(R)-2-((S)-4-tert-Butoxycarbonyl-4-{2-fluoro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester

Base Information

• Chemical Name: (R)-2-((S)-4-tert-Butoxycarbonyl-4-{2-fluoro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester
• CAS No.: 145789-03-3
• Molecular Formula: C₄₂H₅₄FN₅O₉
• Molecular Weight: 791.917
• Mol file: 145789-03-3.mol

Synonyms:(R)-2-((S)-4-tert-Butoxycarbonyl-4-{2-fluoro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester

Chemical Property of (R)-2-((S)-4-tert-Butoxycarbonyl-4-{2-fluoro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((S)-4-tert-Butoxycarbonyl-4-{2-fluoro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester

There total 9 articles about (R)-2-((S)-4-tert-Butoxycarbonyl-4-{2-fluoro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-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: 82.0%

4--N-prop-2-ynylamino>-2-fluorobenzoic acid, trifluoroacetate salt + L-γ-glutamyl-D-glutamic acid tris(1,1-dimethylethyl)ester (145817-20-5) → (R)-2-((S)-4-tert-Butoxycarbonyl-4-{2-fluoro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester (145789-03-3)

Guidance literature:

With triethylamine; diethyl dicarbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2.16667h;

DOI:10.1021/jm950471+

Reference yield:

acetic acid tert-butyl ester (540-88-5) → (R)-2-((S)-4-tert-Butoxycarbonyl-4-{2-fluoro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester (145789-03-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 28 percent / 70percent aq. HClO₄ / 48 h / Ambient temperature

2: 1.) N-methylmorpholine, isobutyl chloroformate / 1.) THF, -20 deg C, 10 min, 2.) THF, a) -20 deg C, 10 min, b) RT, 1.5 h

3: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 3 h / Ambient temperature

4: 82 percent / DEPC, Et₃N / dimethylformamide / 2.17 h / 0 - 20 °C

With 4-methyl-morpholine; perchloric acid; hydrogen; triethylamine; diethyl dicarbonate; isobutyl chloroformate; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm950471+

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (R)-2-((S)-4-tert-Butoxycarbonyl-4-{2-fluoro-4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester (145789-03-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / conc. H₂SO₄ / CH₂Cl₂ / 72 h / Ambient temperature

2: 1.) N-methylmorpholine, isobutyl chloroformate / 1.) THF, -20 deg C, 10 min, 2.) THF, a) -20 deg C, 10 min, b) RT, 1.5 h

3: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 3 h / Ambient temperature

4: 82 percent / DEPC, Et₃N / dimethylformamide / 2.17 h / 0 - 20 °C

With 4-methyl-morpholine; sulfuric acid; hydrogen; triethylamine; diethyl dicarbonate; isobutyl chloroformate; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm950471+

upstream raw materials:

L-γ-glutamyl-D-glutamic acid tris(1,1-dimethylethyl)ester

acetic acid tert-butyl ester

D-Glutamic acid

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