(2S)-2-(4-oxo-4H-quinazolin-3-yl)-propionic acid tert-butyl ester → (2s)-2-(4-Oxo-4h-quinazolin-3-yl)-propionic acid

HRID 2065495Notes

Reaction equation

HRID 2065495 reaction equation
C([O:5][C:6](=[O:20])[C@@H:7]([N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10]1)[CH3:8])(C)(C)C>C(O)(C(F)(F)F)=O>[O:19]=[C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]1[C@@H:7]([CH3:8])[C:6]([OH:20])=[O:5]

Participants

3

Reactant 1

HCID 66650130(2S)-2-(4-oxo-4H-quinazolin-3-yl)-propionic acid tert-butyl ester

Product 1

HCID 771110(2s)-2-(4-Oxo-4h-quinazolin-3-yl)-propionic acidYield 142.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (2S)-2-(4-oxo-4H-quinazolin-3-yl)-propionic acid tert-butyl ester (1.434 g, 5.23 mmol) in TFA (25 mL) was stirred at room temperature for 5 h. The mixture was concentrated under reduced pressure and the residue was dissolved in dry DCM. This process was repeated several times to remove excess TFA. The gum was triturated with diethyl ether, filtrated and washed several times with diethyl ether to afford the sub-title compound as a white powder (1.626 g, 94%): 1H NMR (400 MHz DMSO-d6) δ 1.67 (3H, d), 5.26 (1H, q), 7.58 (1H, m), 7.71 (1H, d), 7.87 (1H, m), 8.15 (1H, m), 8.44 (1H, s).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dry DCM
  3. customto remove excess TFA
  4. customThe gum was triturated with diethyl ether
  5. filtrationfiltrated
  6. washwashed several times with diethyl ether

Sources & evidence

ORD record
ord-36588b096df44007b62b2f4efd4e4297
Source dataset
uspto-grants-2012_10
Patent number
US08288537B2

Reaction notes

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