Benzoyl Peroxide → HCID 70571125, compound

Participants

Reaction Steps

(5R)-7-Oxo-3-vinyl-4-oxa-1-azabicyclo[3.2.0] hept-2-ene (2.5 mmole) in dry tetrahydrofuran (20 ml) was treated with p-mercaptophenol (650 mg) and benzoyl peroxide (10 mg). The resulting solution was stirred under dry nitrogen while being irradiated using a 200 W bulb placed 1" from the reaction vessel for 1 hour. (The temperature of the solution was 25°-30° during this period). The mixture was diluted with ethyl acetate (100 ml) and was washed with water (3×30 ml) and saturated brine (30 ml). The solution was dried (magnesium sulphate) and the solvent was evaporated under reduced pressure to yield a pale yellow gum. The gum was chromatographed on silica gel using ethyl acetate/petroleum ether (b.p. 60°-80°) to give the title compound as a colourless waxy solid (125 mg), [α]D20 =+138.5° (c 1.0, CHCl3), (Found: M+, 263.0585; C13H 13 NO3S requires 263.0616). νmax (CHCl3): 3200, 1790, 1695, 1600, 1580, 1495 cm-1. δ (CDCl3): 2.62 (1H, d, J 16 Hz), 3.10-3.65 (4H, complex), 4.24 (1H, d, J 14 Hz), 4.39 (1H, t, J 7 Hz), 5.25 (1H, d, J 2 Hz), 6.5-6.8 (3H, m), 7.15-7.35 (2H, m). m/e: 263 (M+, 9%), 138 (100), 126 (25), 125 (23), 96 (42).

Provenance & Evidence