Water → 1H-Imidazole-2-propanol, 1-(2-((aminocarbonyl)oxy)ethyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-, carbamate (ester)

Participants

Reaction Conditions

Reaction Steps

In 5 ml of dry acetonitrile was dissolved 240 mg (0.6 mmol) of the diol (137d), and after the solution was cooled to -40° C., 400 mg (2.11 mmol) of trichloroacetyl isocyanate was added dropwise. After 5 minutes, the temperature was elevated gradually to room temperature arid the mixture was stirred for 1 hour. To the mixture was added 3 ml of water and 1.5 ml of triethylamine and the mixture was heated at 50° C. for 3 hours. The reaction mixture was diluted with ice-water and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate-n-hexane to provide 127 mg (yield 43%) of Compound I-151 as crystals. mp 155-163° C. 1H-NMR (CDCl3 -TMS) δ ppm: 1.26(d,J=7.0 Hz,6H),2.16(m,2H),2.86 (m,2H),3.07(sept,1H),4.14(m ,6H),4.88(brs,4H),6.78(m,2H), 7.11 (m,1H); Elementary analysis (C19H24Cl2N4O4S); Calc. (%): C,48.00,H,5.09,Cl,14.92,N,11.79,S,6.74; Found (%): C,47.96,H,5.19,Cl,14.64,N,11.52,S,6.71.

Provenance & Evidence