反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
Under nitrogen atmosphere, to a stirred mixture of (2R*,3S*)-3-hydroxy-4,4-dimethyl-2-(5-phenyl-pentoxy-carbonylamino)-pentanoic acid (0.346 g, 0.98 mmol) in dry CH2Cl2 (45 mL), at 0° C., Et3N (0.41 mL, 2.95 mmol) and subsequently TBTU (0.38 g, 1.20 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. The organics were then removed under reduced pressure, and the resulting crude product purified by column chromatography, using a Teledyne ISCO apparatus, eluting with Cy:AcOEt (from 90:10 to 70:30) to afford the pure title compound (0.125 g, 38%), as white solid. MS (ESI) m/z: 351 [M−NH4]+; (ESI) m/z: 332 [M−H]−. 1H NMR (DMSO-d6) δ 0.93 (s, 9H), 1.34 (h, J=6.37, 7.16 Hz, 2H), 1.53-1.65 (m, 4H), 2.57 (t, J=7.69 Hz, 2H), 4.02 (q, J=6.25 Hz, 2H), 4.36 (d, J=6.24 Hz, 1H), 5.56 (dd, J=6.32, 8.47 Hz, 1H), 7.07-7.34 (m, 5H), 8.38 (d, J=8.48 Hz, 1H).
WORKUP
后处理
- waitThe mixture was left
- customThe organics were then removed under reduced pressure
- customthe resulting crude product purified by column chromatography
- washeluting with Cy