Diisopropylethylamine → HCID 86730166, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-methyl 2-aminopropanoate (270 mg, 2.0 mmol, 1.2 equv. in 10 ml of DMSO) and (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (430 mg, 1.8 mmol, 1.0 equv.) was added DIPEA (805 mg, 6.23 mmol, 3.5 equiv), and the reaction mixture was heated at 110° C. for 120 min. The reaction mixture was poured into water (40 ml) and extracted with EtOAc (2×30 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3×8 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (ethyl acetate in heptane 10 to 80%) to provide (S)-methyl 2-((4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)amino)propanoate (260 mg, white solid) in 47.4% yield. LCMS m/z 309.1 (M+H)+ RT=1.53 min.

Provenance & Evidence