Sodium Hydroxide → HCID 11441991, compound

Participants

Reaction Steps

To a stirred solution of the title D compound, (R)-1-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenylsulfanylcarbonyl]-pyrrolidine-2-carboxylic acid ethyl ester (1.5 g, 3.22 mmol) in methanol (15 mL) is added sodium hydroxide (0.26 g, 6.44 mmol) in water (10 mL) at RT. The reaction mixture is stirred for 4 h. The reaction mixture is concentrated at reduced pressure, poured into water, the aqueous layer is separated, washed with ethyl acetate twice, acidified with concentrated HCl and extracted three times with ethyl acetate. The combined ethyl acetate extract is concentrated and triturated with 1:1 methyl-t-butyl ether and hexane to give (R)-1-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenylsulfanylcarbonyl]-pyrrolidine-2-carboxylic acid as a white solid.

Provenance & Evidence