Diphosgene → (R)-cyclohexyl-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-acetic acid methyl ester

HRID 388448Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[C@H:4]([NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.Cl[C:23](OC(Cl)(Cl)Cl)=[O:24]>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[N:11]1[C:12](=[O:20])[C:13]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:19][C:23]1=[O:24]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (R)-(2-amino-benzoylamino)-cyclohexyl-acetic acid methyl ester (1.08 g, 3.72 mmol) in THF (30 mL) is added trichloromethyl chloroformate (550 mg, 2.78 mmol). The mixture is stirred at 90° C. for 4 hours. The reaction mixture is allowed to cool to room temperature, diluted with EtOAc (100 mL) and washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate and is concentrated to give the desired (R)-cyclohexyl-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-acetic acid methyl ester (1.17 g, 99%).

Workup

temperatureto cool to room temperature
washwashed with H2O (50 mL×3)
dry with materialThe organic layer is dried over sodium sulfate
concentrationis concentrated

Sources & evidence

ORD record: ord-9b102b44cac646f3aa345e346fdec5e0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377949B2

Reaction notes

Loading…