Hydrochloric Acid → HCID 59202200, compound

Participants

Reaction Steps

2-[4-(3-Oxothiolan-2-ylmethyl)phenyl]propionic acid (100 mg) obtained in Example 26 was dissolved in methanol (3.0 ml), and to the solution was added concentrated hydrochloric acid (0.3 ml), and then sodium cyanoborohydride (50 mg) was added. The mixture was stirred overnight, then concentrated under reduced pressure, and extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was dissolved in methanol (3.0 ml), and to the solution was added aqueous lithium hydroxide monohydrate (16 mg, 2.0 ml). The mixture was stirred for 30 minutes, then concentrated under reduced pressure, then the residue was acidified with diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give isomers of the title compound, compounds of Example 27-A (colorless crystals, 21 mg, 21%) and Example 27-B (colorless oil, 44 mg, 44%).

Provenance & Evidence