Diisopropylethylamine → (s)-2-(3-Adamantan-2-yl-ureido)-3,3-dimethyl-butyric acid methyl ester

Participants

Reaction Steps

L-(+)-Methyl-tert-leucinate hydrochloride (564 mg) was dissolved in abs. DMF and then N-ethyl-diisopropylamine (0.68 mL) was added drop by drop. The mixture was allowed to stir for 30 minutes at RT and then 2-adamantyl isocyanate (500 mg) was added in one portion. Stirring was continued over night at RT. The reaction mixture was evaporated to dryness and residual DMF was removed by co-evaporation with toluene. The residue was purified by flash chromatography using 5% methanol in DCM as an eluent to give (S)-2-(3-adamantan-2-yl-ureido)-3,3-dimethyl-butyric acid methyl ester (834 mg) as a white solid. MS (EI): 322.4 (M+).

Provenance & Evidence