Carbidopa → 2,6-Dimethyl-benzoic acid 5-(2-carboxy-2-hydrazino-propyl)-2-hydroxy-phenyl ester

Participants

Reaction Steps

To a solution of carbidopa (732 mg, 3 mmol) in trifluoroacetic acid (10 mL), was slowly added 2,6-dimethyl-benzoyl chloride (504 mg, 3 mmol) at 0° C. and the mixture stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure. The oily residue was dissolved in acetonitrile/H2O and purified by reverse phase preparative HPLC to afford 196 mg of compound 125 [1H NMR (CD3OD, 400 MHz) 1.49 (s, 3H), 2.45 (d, 6H), 3.10 (dd, 2H), 6.82–7.25 (m, 6H). MS (ESI) m/z 359.23 (M+H+)] and 161 mg of compound 126 [1H NMR (CD3OD, 400 MHz): 1.45 (s, 3H), 2.42 (d, 6H), 3.15 (dd, 2H), 6.74–7.27 (m, 6H). MS (ESI m/z 359.23 (M+H+)].

Provenance & Evidence