5-[2-[(Butylamino)carbonyl]-3-methylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester → Ammonium Hydroxide

Participants

Reaction Steps

5-[2-[(Butylamino)carbonyl]-3-methylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester (171 mg, 0.366 mmol) was dissolved in an HCl/dioxane solution (1.37 mL, 4N HCl) at 0° C. and allowed to stand for two h. The solution was concentrated in vacuo. Silica gel chromatography (35:5:0.1 CH2Cl2 :MeOH:NH4OH) of the concentrate afforded the title compound as the free base (88.5 mg, 74%) which was subsequently converted to the hydrochloride salt. The free base was dissolved in MeOH (10 mL) and treated with 1N HCl (0.27 mL) for one h. The reaction was concentrated in vacuo, diluted with water, filtered and lyophilized to afford the title compound (72 mg, 54%).

Provenance & Evidence