Trifluoroacetic acid → HCID 57172084, compound

Participants

Reaction Steps

To a solution of S--(t-Butoxycarbonyl)methyl--N--[4-(4-fluorophenoxy)benzenesulfonyl]-D-penicillamine (188.8 mg, 0.367 mmol) in 3.4 mL of dichloromethane at 20° C. was added trifluoroacetic acid (0.85 mL). The solution was stirred for 16 h and concentrated in vacuo. The residue was partitioned between ethyl acetate (25 mL) and 1 M aq. phosphate buffer (pH 7). The aqueous layer was extracted with two additional portions of ethyl acetate (25 mL), and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue was triturated with diethyl ether (5 mL) to give 67 mg (40%) of S-Carboxymethyl--N--[4-(4-fluorophenoxy)benzenesulfonyl]-D-penicillamine as an off-white solid: mp 69° C.; 1H--NMR (DMSO-d6) δ 1.32 (br s, 6H), 3.25-3.5 (br m, 3H), 7.12 (d, J=8 Hz, 2H), 7.2-7.5 (m, 4H), 7.82 (d, J=8 Hz, 2H), 8.00-8.40 (br s, 1H), 12.5-13.2 (v br s, 1H).

Provenance & Evidence