1,1'-Carbonyldiimidazole → tert-Butyl (2S)-2-{[(4-oxo-3,4-dihydroquinazolin-7-yl)carbonyl]amino}propanoate

HRID 353467Notes

Reaction equation

HRID 353467 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=O)=[CH:9][CH:10]=2)[N:5]=[CH:4][NH:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:27]([O:31][C:32](=[O:36])[C@H:33]([CH3:35])[NH2:34])([CH3:30])([CH3:29])[CH3:28]>O1CCCC1>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([NH:34][C@@H:33]([CH3:35])[C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:36])=[O:14])=[CH:9][CH:10]=2)[N:5]=[CH:4][NH:3]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 89016L-Alanine 1,1-dimethylethyl esterHCID 1354835884-Oxo-3,4-dihydroquinazoline-7-carboxylic acid

Product 1

HCID 135436584tert-Butyl (2S)-2-{[(4-oxo-3,4-dihydroquinazolin-7-yl)carbonyl]amino}propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-oxo-3,4-dihydro-quinazoline-7-carboxylic acid in tetrahydrofuran, 1.2 equivalents of 1,1′-carbonyldiimidazole are added and the mixture is stirred for 30 minutes. Then, the (S)-L-Alanine tert-butyl ester is added and the mixture is stirred for 24 hours until disappearance of starting material. The solvent is removed under reduced pressure and the crude is diluted in chloroform and brine. The organic layer is washed with water and dried over MgSO4. The filtrate is concentrated and the residue is purified by column chromatography to give the desired compound.

Workup

  1. stirringthe mixture is stirred for 24 hours until disappearance of starting material
  2. customThe solvent is removed under reduced pressure
  3. additionthe crude is diluted in chloroform
  4. washThe organic layer is washed with water
  5. dry with materialdried over MgSO4
  6. concentrationThe filtrate is concentrated
  7. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-cf68a484e6a9448b8e239b9b9dc32979
Source dataset
uspto-grants-2004_06
Patent number
US06753340B2

Reaction notes

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