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*,3R*)-3-hydroxy-4,4-dimethyl-2-[(4-phenyl-phenyl)-methoxy-carbonylamino]-pentanoic acid and (2R*,3S*)-3-hydroxy-4,4-dimethyl-2-[(4-phenyl-phenyl)-methoxy-carbonylamino]-pentanoic acid (0.203 g, 0.55 mmol) in dry CH2Cl2 (25 mL), at 0° C., Et3N (0.23 mL, 1.65 mmol) and subsequently TBTU (0.21 g, 0.66 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 80:20) to afford the pure title compound (0.063 g, 58%), as pure anti diastereoisomer, as white solid. MS (ESI) m/z: 371 [M−NH4]+; (ESI) m/z: 352 [M−H]−. 1H NMR (DMSO-d6) δ 0.95 (s, 9H), 4.37 (d, J=4.64 Hz, 1H), 4.83 (dd, J=4.65, 8.16 Hz, 1H), 5.14 (s, 2H), 7.32-7.56 (m, 5H), 7.60-7.75 (m, 4H), 8.25 (d, J=8.12 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