Methyl Acetate → HCID 178432570, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 0.1 g (0.26 mmol) of trans-N-Hydroxy-4-[4-(4-isopropyl-piperazine-1-carbonyl)-cyclohexyloxy]-benzamidine and 0.24 g of molecular sieves 4A in 3 ml THF, 17 mg (0.39 mmol, 55% purity) of sodium hydride was added and the mixture was stirred at 60° C. for 45 min. After cooling down, 0.1 ml (1.45 mmol) of methyl acetate was dropwised to the mixture and the mixture was refluxed for 5 hr. After that, 56 mg (1.28 mmol, 55% purity) of sodium hydride and 1 ml (14.5 mmol) of methyl acetate were added to the mixture. The mixture was refluxed for 16 hr. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography on silica gel eluting with dichloromethane and methanol=from 98:2 to 19:1, after that, purified with cyclohexane and ethyl acetate=from 3:1 to 2:1. The combined product fractions were evaporated to dryness to yield 0.022 g (20% yields) of the titled compound. MS (m/e): 413.4 (MH+).

Provenance & Evidence