Tetrahydrofuran → HCID 57513839, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing {1-[1-Benzyl-5-(4-fluoro-phenyl)-1H-[1,2,4]triazol-3-ylcarbamoyl]-1-methyl-ethyl}-carbamic acid benzyl ester (777 mg, 1.59 mmol) was chilled to 0° C. The solid was dissolved in 48% aqueous HBr (5 mL) and the mixture stirred at 0° C. After 10 min the mixture was allowed to warm to room temp. After 5.5 hr THF (5 mL) was added and the mixture was stirred for 2 days. The reaction was diluted with water (30 mL) and extracted with Et2O (2×50 mL). The pH of the aqueous phase was adjusted to 10 by addition of 4N NaOH. The basic aqueous phase was extracted with Et2O (2×50 mL). The organics from the second extraction were combined and dried with brine (15 mL) followed by Na2SO4. Concentration resulted in a brown oil. The oil was dissolved in EtOAc/MeOH and the solvent evaporated to yield the title compound as a white solid: 1H NMR (400 MHz, ACETONITRILE-d3) 1.53 (s, 6H) 5.38 (s, 2H) 7.08-7.19 (m, 2H) 7.19-7.28 (m, 2H) 7.28-7.39 (m, 3H) 7.60-7.69 (m, 2H); Rt (method A)=0.96 min (M+H)+=354.2.

Provenance & Evidence