N-Methylaniline → HCID 57264193, compound

Participants

Reaction Steps

To a 0° C. solution of N-[4-(4-fluorophenoxy)benzenesulfonyl]--S--[2-(methoxycarbonyl)ethyl]-D-penicillamine allyl ester (0.36 g, 0.687 mmol) in 5 mL of ethyl acetate was added N-methylaniline followed by Pd(PPh3)4 (16 mg, 0.014 mmol). After 3 hours, the solution was concentrated, and the residue was purified by chromatography on silica gel, eluting first with 1:1 ethyl acetate:hexane and then with 10% methanol in dichloromethane to give N-[4-(4-fluorophenoxy)benzenesulfonyl]--S--[2-(methoxycarbonyl)ethyl]-D-penicillamine as a white solid in 89% yield: mp 123-124° C.; 1H--NMR(CDCl3) δ 1.27 (s, 3H), 1.35 (s, 3H), 2.40-2.82 (m, 4H), 3.71 (s, 3H), 3.94 (d, 1H, J=11 Hz), 5.60 (d, 1H, J=11 Hz), 6.93-7.82 (m, 8H); FAB HRMS: expected (M+Cs)=618.0033. Found (M+Cs)=618.0038

Provenance & Evidence