Dichloroisoproterenol → HCID 18672513, compound

Participants

Reaction Steps

To a 0° C. solution of 0.048 g (0.16 mmol) triphosgene in 1 mL CH2Cl2 was slowly added a solution of 0.1 g 0.48 mmol) N-(4-amino-benzyl)-2,2-dimethyl-propionamide and 0.07 mL (0.5 mmol) triethylamine in 8 mL CH2Cl2 over 20 min. The reaction mixture was allowed to warm to room temperature for 15 min., then recooled to 0° C. whereupon a solution of 0.2 g (0.9 mmol) 2-methylamino-1-(3,4-dichlorophenyl)ethanol (prepared as in scheme 1, step 2) and 0.1 mL (0.5 mmol) triethylamine in 2 mL CH2Cl2 was added. The reaction mixture was allowed to warn to room temperature and stir 1 hour, then diluted with 100 mL EtOAc, washed with 100 mL each of, saturated aqueous NaHCO3, 10% aqueous KHSO4, and brine, then dried over Na2SO4, filtered and concentrated. Purification by flash chromatography (2.5×12 cm silica gel, linear gradient 3-5% MeOH/CH2Cl2) afforded 0.14 g N-(4-{3-[2-(3,4-Dichloro-phenyl)-2-hydroxy-ethyl]-3-methyl-ureido}-benzyl)-2,2-dimethyl-propionamide. 1H NMR(300 mHz, CD3OD) δ 7.61 (d, 1H, J=1.83 Hz); 7.49 (d, 1H, J=8.24 Hz); 7.35 (dd, 1H, J=1.83 and 8.24 Hz); 7.26 (d, 2H, J=8.54 Hz); 7.17 (d, 2H, J=8.55 Hz); 4.93 (m, 1H); 4,31 (s, 2H); 3.54 (m, 2H); 2.96 (s, 3H); 1.20 (s, 9H).

Provenance & Evidence