Acetic Acid → N-[3-(Methylsulfanyl)-2-oxoazetidin-3-yl]-2-phenoxyacetamide

Participants

Reaction Steps

A solution of (24) (516 mg) in dry tetrahydrofuran (THF) (10 ml) was cooled to -10° C. and treated with tetrabutylammonium fluoride (476 mg) and glacial acetic acid (180 mg) in a minimum volume of dry THF. After approximately 15 mins the mixture was poured into a mixture of ethyl acetate and water. The organic phase was separated and washed successively with dilute sodium bicarbonate, dilute hydrochloric acid, and brine, then dried and evaporated. Chromatography on silica gel gave the product (25) (366 mg), a white solid. νmax 3410, 1775 and 1690 cm-1 ; δppm (CDCl3) (90 MHz) 2.24 (s, 3 H), 3.48 and 3.90 (ABq, 2H, J7.0 Hz), 4.50 (s, 2H), 6.24 (s, 1H, exch.), 6.80 to 7.45 (m, 6H, becomes m, 5H, on exch.)

Provenance & Evidence