Hydrochloric Acid → HCID 86614676, compound

Participants

Reaction Steps

To a stirred mixture of N-(trifluoroacetyl)-L-alanine (5.05 g, 27.3 mmol) and pyridine (0.3 mL) was added oxalyl chloride (7.62 g, 60 mmol) at 0° C. under a nitrogen atmosphere. The reaction mixture was then allowed to warm to room temperature and stirred for an additional 2 hrs. The reaction mixture was then concentrated under reduced pressure to provide an oil that was combined with 8 mL of thioanisole. The resulting solution was then added a solution of AlCl3 (76 mmol, about 2.8 eq. relative to the N-(trifluoroacetyl)-L-alanine, about 10 g) in thioanisole (7 mL) at 0° C. The resulting reaction mixture was then allowed to warm to room temperature and stirred for about 14 hrs. After stirring, the reaction mixture was poured into cold 1 N aqueous hydrochloric acid (200 mL) and the resulting mixture extracted with ethyl acetate (200 mL), the ethyl acetate dried (Na2SO4), and the ethyl acetate removed under reduced pressure to provide a residue that was purified by flash chromatography using a silica gel column eluted with ethyl acetate/hexane in a ratio of 1:9 to provide S (−)-2-[N-(trifluoroacetyl)amino]-1-(4-methylthiophenyl)-1-propanone (B) (35% yield).

Provenance & Evidence