2-(2-Carboxyethyl)-3-(2-chlorophenyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid ethyl ester → 3-(2-Chlorophenyl)-2-(2-ethylcarbamoylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic Acid Ethyl Ester

HRID 1039367Notes

Reaction equation

HRID 1039367 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:30])=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12]=[C:11]([CH2:17][CH2:18][C:19](O)=[O:20])[N:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])[C:9]2=[O:29])=[O:5])[CH3:2].C(OC(C1C(C)=[C:38]2C(=CC=1C)N=C(CCC(OCC)=O)[N:40](C1C=CC=CC=1Cl)[C:39]2=O)=O)C>C(O)C.[OH-].[Na+]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:30])=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12]=[C:11]([CH2:17][CH2:18][C:19](=[O:20])[NH:40][CH2:39][CH3:38])[N:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])[C:9]2=[O:29])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 671751102-(2-Carboxyethyl)-3-(2-chlorophenyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid ethyl esterHCID 671755223-(2-Chlorophenyl)-2-(2-ethoxycarbonylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid ethyl ester

Product 1

HCID 115906083-(2-Chlorophenyl)-2-(2-ethylcarbamoylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic Acid Ethyl Ester

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 702EthanolSolvent

Procedure

2-(2-Carboxyethyl)-3-(2-chlorophenyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid ethyl ester: A solution of 3-(2-chlorophenyl)-2-(2-ethoxycarbonylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid ethyl ester (0.1 g, 0.22 mmol) in absolute ethanol (6 mL) is treated with 2M sodium hydroxide solution (12 drops) and the reaction mixture is stirred at room temperature for 4 days. The solvent is removed under reduced pressure, and the residue is dissolved in water and washed with ethyl acetate. The aqueous layer is acidified to pH2 with concentrated hydrochloric acid and this is extracted with ethyl acetate. The organic phases are combined, dried over anhydrous MgSO4 and the solvent is removed under reduced pressure to afford the title compound, which is used without further purification.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue is dissolved in water
  3. washwashed with ethyl acetate
  4. extractionthis is extracted with ethyl acetate
  5. dry with materialdried over anhydrous MgSO4
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-d23d3ea4678b471b9188a0b9bb8020b5
Source dataset
uspto-grants-2013_10
Patent number
US08552015B2

Reaction notes

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