1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating 2: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 3: 2.5 h / ice-bath View Scheme

1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating 2: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 3: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 5: TFA / CH2Cl2 6: EDC / dimethylformamide / 40 °C 7: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature View Scheme

1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating 2: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature View Scheme

hydrogen; palladium on activated charcoal in ethyl acetate T=20°C; 1 h;