Réaction #51888

Équation de réaction

di-tert-butyl L-glutamate hydrochloride

Et3N

2,3,4,5-tetrafluorobenzoyl chloride

→

di-tert-butyl (2,3,4,5-tetrafluorobenzoyl)-L-glutamate

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   LavageSixteen hours later the solution was washed with H2O
2. 2
   Séchagedried (MgSO4)
3. 3
   Autreevaporated to dryness

Mode opératoire

To an ice-cold solution of di-tert-butyl L-glutamate hydrochloride (6.6 g, 22.4 mmol) and Et3N (6.9 ml, 50 mmol) in dry CH2Cl2 (70 ml) was added, over a period of 1.5 hr, 2,3,4,5-tetrafluorobenzoyl chloride (5.0 g, 23.5 mmol) in dry CH2Cl2 (20 ml) and thirty minutes later the solution was allowed to warm to room temperature. Sixteen hours later the solution was washed with H2O, dried (MgSO4) and evaporated to dryness. 1H NMR δ 1.40+1.42 (2s, 18H, t-butyl), 1.85+1.95 (2m, 2H, CH2CH), 2.34 (t, 2H, CH2CO, J=7.5 Hz), 4.3 (m, 1H, CH), 7.57 (m, 1H, H6), 8.80 (d, 1H, NH, J=7.5 Hz); 19F NMR δ −138.6+139.0 (2m, 2F, F2+5), −152.4 (m, 1H, F4), −154.9 (t, 1F, F3, J=20 Hz).

Source