Ethyl Acetate → HCID 53866326, compound

Participants

Reaction Steps

To a solution of 281 mg (0.5 mmol) of benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-3-methyl-4-bromo-2-butenoate in 10 ml of methanol at 0° was added 207 mg (1 mmol) of silver perchlorate. The reaction mixture was stirred for 1 hour. A large amount of ethyl acetate was added. The resulting solution was washed thoroughly with brine, dried, and evaporated in vacuo to dryness to provide a mixture of the title product and benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-2-methoxy-3-methyl-3-butenoate. The products were separated by preparative thin layer chromatography (silica gel plates developed with 1:1/hexane:ethylacetate). A purified sample of 46 mg of the title product was isolated: nmr (CDCl3) δ 2.20 (s, 3, CH3), 3.25 (s, 3, OCH3), 4.37 (s, 2, CH2OCH3), 3.73 (t, 1) and 3.50 (q, 1) [C4 --H], 4.97 (m, 1, C3 --H), 4.47 (s, 2, side chain CH2) and 7.2 (b, ArH).

Provenance & Evidence