Diisopropylethylamine → S-methyl--N--[4-(phenoxy)benzenesulfonyl]-D-penicillamine methyl ester

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Reaction Steps

To a solution of S-methyl-D-penicillamine methyl ester (0.160 g., 0.904 mmol) and diisopropylethylamine (0.172 mL, 0.99 mmol) in dichloromethane (3 mL) was added 4-phenoxybenzenesulfonyl chloride (0.304 g, 1.13 mmol) via solid addition funnel. After 2.5 hours at room temperature, the solution was concentrated and the residue was purified on silica, eluting with 20% ethyl acetate in hexane, to give S-methyl--N--[4-(phenoxy)benzenesulfonyl]-D-penicillamine methyl ester as a white solid in 87% yield: 1H NMR (CDCl3) δ 1.31 (s, 3H), 1.37 (s, 3H), 1.96 (s,3H), 3.48 (s, 3H), 3.79 (d, 1H, J=9 Hz), 5.34 (d, 1H, J=10 Hz), 6.99-7.79 (m, 9H); FAB HRMS: expected (M+Na)=432.0915, found (M+Na)=432.0907.

Provenance & Evidence