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
To a stirred mixture of (2R,3S)-3-hydroxy-2-[methyl-(5-phenylpentoxycarbonyl)-amino]-butanoic acid (0.04 g, 0.14 mmol) in dry CH2Cl2(5.0 mL), under nitrogen atmosphere at 0° C., Et3N (0.06 mL, 0.41 mmol) and subsequently TBTU (0.05 g, 0.17 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. Upon full conversion of the starting material, the organics were removed under reduced pressure, and the resulting crude product absorbed over silica gel and purified by column chromatography, eluting with Cy:EtOAc (from 100:0 to 0:100) to afford the title compound (0.01 g, 23%), as a mixture of two rotamers (1:1.5 ratio), as a colorless oil. [α]25D −16.66 (c 0.1, CHCl3). 1H NMR (DMSO-d6) δ 1.29-1.41 (m, 10H), 1.53-1.69 (m, 8H), 2.58 (t, J=7.6 Hz, 4H), 2.93 (s, 6H), 3.98-4.11 (m, 4H), 4.77-4.89 (m, 2H), 5.24-5.33 (m, 1H, major rotamer), 5.35-5.43 (m, 1H, minor rotamer), 7.13-7.32 (m, 10H).
WORKUP
后处理
- waitThe mixture was left
- customUpon full conversion of the starting material, the organics were removed under reduced pressure
- customthe resulting crude product absorbed over silica gel
- custompurified by column chromatography
- washeluting with Cy