反应 #5514

反应方程式

Methyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate

Lithium hydroxide monohydrate

hydrochloric acid

→

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

反应条件

后处理

1. 1
   其他degassed tetrahydrofuran (10 ml) and water (5 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 (Na2SO4)
5. 5
   其他the solvent is evaporated

实验过程

Methyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate (Isomer B) (0.16 g, 0.44 mmol) is partially dissolved in nitrogen degassed tetrahydrofuran (10 ml) and water (5 ml). Lithium hydroxide monohydrate (0.056 g, 1.33 mmol) is added and the mixture is stirred at room temperature for 3 hours. 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 (Na2SO4) and the solvent is evaporated to give (3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid (Isomer B), m.p. 169°-173° C.; the more active NEP inhibiting isomer.

来源