4-Methylmorpholine → HCID 86757295, compound

Participants

Reaction Steps

A solution of 0.269 g of 2-(trimethylsilyl)ethyl-1-isocyanato-1-cyclohexane carboxylate and 0.403 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-4-methylvalerohydrazide in 6 ml of a 5:1 mixture of dichloromethane and dimethylformamide was treated with 0.15 ml of N-methylmorpholine and was stirred for 2 hours at room temperature. The solution was then washed with 5% citric acid solution and then saturated sodium chloride solution, dried over anhydrous magnesium sulphate and evaporated. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (2:1) followed by hexane/ethyl acetate (1:1) for the elution. The product obtained was dissolved in 5 ml of tetrahydrofuran and 1.6 ml of a 1.0M solution of tetrabutylammonium fluoride in tetrahydrofuran added. The mixture was stirred for 1.5 hours at room temperature, then diluted with ethyl acetate and washed successively with 5% citric acid and brine, dried and evaporated. The residue was triturated with ether and there was obtained 0.25 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-4-methyl-N-(2,4-dioxo-1,3-diazaspiro[4.5]decan-3-yl)valeramide in the form of a white solid.

Provenance & Evidence