Hydrochloric Acid → HCID 86591690, compound

Participants

Reaction Steps

A mixture of ethyl 3-[2-amino-4-(5,6,7,8-tetrahydro-2-naphthyl)-5-thiazolyl]propionate (270 mg), [4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]phenyl]acetic acid (250 mg), WSC (170 mg), HOBt (135 mg) and N,N-dimethylformamide (10 ml) was stirred for 3 days. The reaction mixture was poured into water, neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was dissolved in ethanol (9 ml)-tetrahydrofuran (1 ml) and 1N aqueous sodium hydroxide solution (2 ml) was added at 0° C. The mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into water, neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 3-[2-[[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]phenyl]acetylamino]-4-(5,6,7,8-tetrahydro-2-naphthyl)-5-thiazolyl]propionic acid (270 mg,57%) was obtained as an amorphous oil from a fraction eluted with acetone-hexane (3:2, volume ratio).

Provenance & Evidence