Water → Benzyl 6-benzyl-3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

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Reaction Steps

A solution of benzyl 6-benzyl-3-ethylthio-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (98) (0.047 g) in chloroform (5 ml) was treated with water (0.005 g), pyridine (0.033 g) and iodobenzene dichloride (0.082 g) at 0° under argon. The solution was concentrated after 2 hours and then chromatographed on silica gel 60 (<230 mesh) eluting with ethyl acetate/60°-80° petroleum ether 7:3 to give benzyl 6-benzyl-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (79) (0.030 g); m.p. 118°-123° (ethyl acetate/60°-80° petroleum ether); νmax (CHCl3) 2980, 1775 and 1745 cm-1 ; τ(CDCl3) 2.6-2.9 (10H, m, phenyls), 4.89 (2H, s, OCH2) 4.98 (1H, s, C2-H), 5.92 (1H, ddd J 8, 3 and 2 Hz, C5-H), 6.26 (1H, ddd J 9, 6 and 3 Hz, C6-H), 6.6-7.3 (5H, m, C4-H, C8-H2, SCH2), 7.72 (1H, dd J 15 and 2 Hz, C4-H) and 8.68 (3H, t J 71/2 Hz, CH3).

Provenance & Evidence