Acetic Acid → 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(1,6-naphthyridin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoic acid

Participants

Reaction Steps

The compound from Step 2 (280 mg) was hydrolyzed by dissolving it in THF (3 mL), MeOH (1.5 mL), and 2N LiOH (0.27 mL) and heating at 70° C. for 6 hours. The solution was cooled to room temperature, diluted with H2O (50 mL), acidified with glacial AcOH to pH 5 and then diluted with 25% aqueous NH4OAc (50 mL). The mixture was extracted with ethyl acetate (3×50 mL), washed with brine (50 mL), and dried (MgSO4). The solution was evaporated to dryness and coevaporated with toluene (50 mL) to provide the title acid as a white solid; m.p. 204° C. (dec.).

Provenance & Evidence