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

HRID 602930Notes

Reaction equation

HRID 602930 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-abeef2e52a3d41b093c4cf8b2badb8d9
Source dataset
uspto-grants-2011_03
Patent number
US07906650B2

Reaction notes

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