m-Chloroperbenzoic acid → HCID 57295905, compound

Participants

Reaction Steps

To a solution of 60 mg of 3-(2'-acetamidoethylthio)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, 1-naphthylmethyl ester, in 10 mL of methylene chloride at -50° under argon was added a solution of 32 mg of m-chloroperbenzoic acid in 3 mL of methylene chloride in one portion. This solution was stirred for 30 min at -40° and then allowed to warm to room temperature over a 30 min period. The methylene chloride solution was washed sequentially with aqueous sodium sulfite and aqueous sodium bicarbonate (2X), dried over sodium sulfate and evaporated to dryness. The crude product was purified by preparative thin layer chromatography on a 20×20×0.2 cm silica gel plate, eluted with 5% methanol in methylene chloride, to afford 55 mg (88%) of 3-(2'acetamidoethylsulfinyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, 1-naphthylmethyl ester, as a glassy mixture of 2 diastereoisomers (at sulfur). IR (Nujol mull): 3250, 1785, 1715, 1670 cm-1 ; NMR (220 MHz; CDCl3): δ 1.93 (3H, s), 2.8-3.7 (9H, m), 4.66 (1H, m), 5.5-5.75 (2H, m), 6.48 (1H, m), and 7.3-1.1 (7H, m); MS (field desorption) confirmed molecular weight of 425. ##STR23##

Provenance & Evidence