L-Glutamic acid, N-[4-[[(1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2 ,3-difluorobenzoyl]-, diethyl ester

Base Information

• Chemical Name: L-Glutamic acid, N-[4-[[(1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2 ,3-difluorobenzoyl]-, diethyl ester
• CAS No.: 141412-67-1
• Molecular Formula: C27H30F2N4O6
• Molecular Weight: 544.555
• Mol file: 141412-67-1.mol

Synonyms:

Chemical Property of L-Glutamic acid, N-[4-[[(1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2 ,3-difluorobenzoyl]-, diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Glutamic acid, N-[4-[[(1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2 ,3-difluorobenzoyl]-, diethyl ester

There total 7 articles about L-Glutamic acid, N-[4-[[(1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2 ,3-difluorobenzoyl]-, diethyl 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: 69.0%

4(3H)-oxo-6-(bromomethyl)-2-methyl quinazoline (112888-43-4) + diethyl N-(2,3-difluoro-4-(methylamino)benzoyl)-L-glutamate (141412-59-1) → diethyl N-(2,3-difluoro-4-(N-((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)benzoyl)-L-glutamate (141412-67-1)

Guidance literature:

With caesium carbonate; In acetonitrile; at 60 ℃; for 24h;

DOI:10.1021/jm00090a024

Reference yield:

diethyl-L-glutamate hydrochloride (1118-89-4) → diethyl N-(2,3-difluoro-4-(N-((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)benzoyl)-L-glutamate (141412-67-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 2 h

2: 96 percent / TFA / 0.5 h / 0 °C

3: 69 percent / Cs₂CO₃ / acetonitrile / 24 h / 60 °C

With caesium carbonate; triethylamine; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1021/jm00090a024

Reference yield:

methyl 4-((tert-butyloxycarbonyl)amino)-2,3-difluorobenzoate (129589-70-4) → diethyl N-(2,3-difluoro-4-(N-((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)benzoyl)-L-glutamate (141412-67-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, 2.) DMF, 2 h

2: 88 percent / aq. NaOH / ethanol / 18 h

3: oxalyl chloride, DMF / CH₂Cl₂ / 1 h

4: Et₃N / CH₂Cl₂ / 2 h

5: 96 percent / TFA / 0.5 h / 0 °C

6: 69 percent / Cs₂CO₃ / acetonitrile / 24 h / 60 °C

With sodium hydroxide; oxalyl dichloride; sodium hydride; caesium carbonate; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; In ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm00090a024

upstream raw materials:

4(3H)-oxo-6-(bromomethyl)-2-methyl quinazoline

diethyl N-(2,3-difluoro-4-(methylamino)benzoyl)-L-glutamate

diethyl-L-glutamate hydrochloride

methyl 4-((tert-butyloxycarbonyl)amino)-2,3-difluorobenzoate

Downstream raw materials:

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