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

HRID 419686Notes

Reaction equation

HRID 419686 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25](=[O:42])[C@@H:26]([N:28]([C:31](=[O:41])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N:38]=[N+]=[N-])[CH:29]=O)[CH3:27])([CH3:23])([CH3:22])[CH3:21]>C1(C)C(C)=CC=CC=1>[C:20]([O:24][C:25](=[O:42])[C@@H:26]([N:28]1[C:31](=[O:41])[C:32]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:38]=[CH:29]1)[CH3:27])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86630400(2S)-2-(N-(2-Azido-benzoyl)-N-formylamino)-propionic acid tert-butyl ester

Product 1

HCID 66650130(2S)-2-(4-oxo-4H-quinazolin-3-yl)-propionic acid tert-butyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Triphenylphosphine (3.41 g, 13.0 mmol) was added portionwise to a solution of (2S)-2-(N-(2-azido-benzoyl)-N-formylamino)-propionic acid tert-butyl ester (3.437 g, 10.80 mmol) in xylene (70 mL) at room temperature. The reaction mixture was stirred at room temperature until the evolution of nitrogen ceased (approx. 1 h), and then refluxed for 20 h. The volatiles were evaporated and the residue was purified by flash chromatography (30% ethyl acetate in hexane) to afford the sub-title compound as a colorless oil (2.221 g, 75%). 1H NMR (400 MHz C6D6) δ 1.30 (3H, d), 1.34 (9H, s), 4.97 (1H, q), 7.08 (1H, m), 7.31 (1H, m), 7.81 (1H, s), 7.86 (1H, d), 8.55 (1H, m).

Workup

  1. custom(approx. 1 h)
  2. temperaturerefluxed for 20 h
  3. customThe volatiles were evaporated
  4. customthe residue was purified by flash chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9e6aa7bbad5e4355bfe0cf09042141c7
Source dataset
uspto-grants-2012_01
Patent number
US08093392B2

Reaction notes

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