1: 69 percent / 1-hydroxybenzotriazole hydrate, N-(N,N'-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, triethylamine / dimethylformamide / 1.) r.t., 2 days; 2.) 50 deg C, 3 h 2: 90 percent / H2 / 5percent palladium on carbon / acetic acid / 2585.7 Torr / Ambient temperature View Scheme

1: 41 percent / 1-hydroxybenzotriazole hydrate, N-(N,N'-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, triethylamine / dimethylformamide / 1.) RT, 2 d, 2.) 50 deg C, 3 h 2: 94 percent / H2 / 5percent Pd/C / acetic acid / 2585.7 Torr / Ambient temperature View Scheme

1: 94 percent / 10percent KOH / methanol / Heating 2: 41 percent / 1-hydroxybenzotriazole hydrate, N-(N,N'-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, triethylamine / dimethylformamide / 1.) RT, 2 d, 2.) 50 deg C, 3 h 3: 94 percent / H2 / 5percent Pd/C / acetic acid / 2585.7 Torr / Ambient temperature View Scheme

1: 1.) NaH / 1.) DMF, RT, 15 min, 2.) overnight 2: 94 percent / 10percent KOH / methanol / Heating 3: 41 percent / 1-hydroxybenzotriazole hydrate, N-(N,N'-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, triethylamine / dimethylformamide / 1.) RT, 2 d, 2.) 50 deg C, 3 h 4: 94 percent / H2 / 5percent Pd/C / acetic acid / 2585.7 Torr / Ambient temperature View Scheme

triethylamine in benzene 5 h;