反应 #5519

反应方程式

Benzyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylate

Lithium hydroxide monohydrate

hydrochloric acid

→

(3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylic acid

反应条件

后处理

1. 1
   其他degassed tetrahydrofuran (5 ml) and water (1 ml)
2. 2
   萃取extracted with ethyl acetate (2×50 ml)
3. 3
   洗涤The combined organic layers are washed with brine (1×50 ml)
4. 4
   干燥dried (MgSO4)
5. 5
   其他the solvent is evaporated
6. 6
   其他The product is triturated from diethyl ether/hexane (1:1)

实验过程

Benzyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylate (Isomer A), (0.11 g, 0.25 mmol) is dissolved in nitrogen degassed tetrahydrofuran (5 ml) and water (1 ml). Lithium hydroxide monohydrate (0.032 g, 0.75 mmol) is added and the mixture is stirred for 3 hours at room temperature. The mixture is poured into 1N hydrochloric acid and extracted with ethyl acetate (2×50 ml). The combined organic layers are washed with brine (1×50 ml), dried (MgSO4) and the solvent is evaporated. The product is triturated from diethyl ether/hexane (1:1) to give (3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylic acid (Isomer A), m.p. 165°-168° C.

来源