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

HRID 388459Notes

Reaction equation

HRID 388459 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])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH: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]([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])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 10426DiphosgeneHCID 68727988(S)-(2-amino-benzoylamino)-phenyl-acetic acid methyl ester

Product 1

HCID 68728966(S)-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl-acetic acid methyl esterYield 61.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (S)-(2-amino-benzoylamino)-phenyl-acetic acid methyl ester (330 mg, 1.16 mmol) in THF (30 mL) is added trichloromethyl chloroformate (115 mg, 0.58 mmol). The mixture is stirred at 90° C. for 16 hours. The reaction mixture is allowed to cool to room temperature, diluted with EtOAc (100 mL) and is washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate and concentrated to give the (S)-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl-acetic acid methyl ester (110 mg, 31%).

Workup

  1. temperatureto cool to room temperature
  2. washis washed with H2O (50 mL×3)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5037b4fe7ba4487c9cd6d30074e825e4
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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