反应详情

Sodium hydride (0.20 mg, 4.9 mmol) is added to a solution of 2-benzyloxycarbonylamino-3-(bromoactyl-prop-2-ynyl-amino)-propionic acid methyl ester (2.0 g, 4.8 mmol) in THF (50 mL) at 0° C. The solution is stirred for 40 minutes then quenched with saturated NH4Cl solution. The reaction mixture is concentrated in vacuo then diluted with CH2Cl2 and washed with brine. The organic layer is dried over, filtered and concentrated in vacuo. The crude product is purified by chromatography eluting with 50% EtOAc/hexanes to give the title product (1.4 g, 4.1 mmol). 1H NMR (CDCl3, 300 MHz) δ7.30 (m, 5H), 5.20 (s, 2H), 5.10 (m, 1H), 4.30 (dd, 1H), 4.25 (d, 2H), 4.08 (m, 1H), 4.00 (dd, 1H), 3.78 (dd, 1H), 3.78 (s, 3H), 2.25 (t, 1H).

1. customthen quenched with saturated NH4Cl solution
2. concentrationThe reaction mixture is concentrated in vacuo
3. additionthen diluted with CH2Cl2
4. washwashed with brine
5. customThe organic layer is dried over,
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude product is purified by chromatography
9. washeluting with 50% EtOAc/hexanes