反应详情

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.

1. customdegassed tetrahydrofuran (10 ml) and water (5 ml)
2. extractionextracted with ethyl acetate (2×50 ml)
3. washThe combined organic layers are washed with brine (1×50 ml)
4. dry with materialdried (Na2SO4)
5. customthe solvent is evaporated