1,1'-Carbonyldiimidazole → (2S)-3-Methyl-2-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-butyric acid tert-butyl ester

HRID 2110822Notes

Reaction equation

HRID 2110822 reaction equation
[C:1]([O:5][C:6](=[O:20])[C@@H:7]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22]>C1COCC1>[C:1]([O:5][C:6](=[O:20])[C@@H:7]([N:11]1[CH2:12][C:13]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:19][C:21]1=[O:22])[CH:8]([CH3:10])[CH3:9])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 66650028HCID 66650028, compound

Product 1

HCID 66650119(2S)-3-Methyl-2-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-butyric acid tert-butyl esterYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-2-(2-amino-benzylamino)-3-methyl-butyric acid tert-butyl ester (1.573 g, 5.65 mmol) in THF (20 mL) was added carbonyldiimidazol (1.008 g, 6.21 mmol) and the reaction was stirred under reflux overnight. The solvent was evaporated and the residue purified by flash chromatography (hexane/ethyl acetate, 50/50) to afford the sub-title compound as a yellow solid (662 mg, 38%). 1H NMR (400 MHz CDCl3) δ 0.95 (3H, d), 1.08 (3H, d), 1.49 (9H, s), 2.32 (1H, m), 4.39 (1H, d), 4.60 (1H, d), 4.72 (1H, d), 6.81 (1H, d), 6.94 (1H, t), 7.07 (1H, d), 7.18 (1H, t), 8.68 (1H, s).

Workup

  1. temperatureunder reflux overnight
  2. customThe solvent was evaporated
  3. customthe residue purified by flash chromatography (hexane/ethyl acetate, 50/50)

Sources & evidence

ORD record
ord-37f294fec7e2489f88225d6e67cfafe9
Source dataset
uspto-grants-2009_04
Patent number
US07517987B2

Reaction notes

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