N-bromobutanimide → HCID 68291092, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-((R)-3-((tert-butoxycarbonyl)amino)-2-methylbutan-2-yl)-4,5-dihydrooxazole-4-carboxylate (2.0 g, 6.36 mmol) in CCl4 (180 mL) was added NBS (3.96 g, 22.27 mmol) at RT. The reaction mixture was heated to 85° C. and stirred for 30 min. It was then diluted with water and extracted with CCl4 (3×50 mL). The combined organic layers were dried over anhydrous Na2SO4 and the solvent was removed under vacuum. Crude product was purified by ELSD combiflash (120 g silica column, 40% EtOAc: Pet-Ether) to afford a white solid (1.2 g, 60.4%). 1HNMR (400 MHz, CDCl3) δ ppm: 1.12 (d, J=6.8 Hz, 3H), 1.408 (s, 15H), 3.89-3.97 (m, 4H), 4.88-4.91 (d, J=10 Hz, 1H), 8.17 (s, 1H). LC retention time: 1.985 min (analytical HPLC Method N).

Provenance & Evidence