Potassium bis(trimethylsilyl)amide → [3-(3-Methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester

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Reaction Steps

Dissolve (3-{[3-(3-fluoro-pyridin-4-yl)-5-methyl-isoxazole-4-carbonyl]-amino}-cyclohexylmethyl)-carbamic acid benzyl ester (0.65 g, 0.0014 mol) in N,N-dimethylformamide (6 mL) at ambient temperature under a nitrogen atmosphere. Add a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene, 3.35 mL, 0.0017 mol) and stir for 15 min. at ambient temperature. Quench the dark mixture with water and follow with the addition of solid sodium chloride. Extract with ethyl acetate and wash the combined extracts with water and dry over sodium sulfate. Concentrate and elute over silica gel with methanol/dichloromethane allowing for the isolation of 0.44 g (71%) of the desired product as an off white solid. MS(S): (M+1)+ 447.2, 448.2 m/z.

Provenance & Evidence