Isobutyl chloroformate → HCID 101153814, compound

Participants

Reaction Conditions

Reaction Steps

N,N-Diisopropylethylamine (4.7 mL, 27 mmol) and isobutyl carbonochloridate (3.11 ml, 23.78 mmol) were added to a solution of (R)-2-((tert-butoxycarbonyl)amino)propanoic acid (3.0 g, 15.9 mmol) in tetrahydrofuran (34.5 ml) at 0° C. and the mixture was stirred at 0° C. for four hours. The mixture was then diluted with acetonitrile (22 mL). TMS-diazomethane (2.0 M in diethyl ether, 15.9 ml, 31.7 mmol) was then added slowly to the mixture at 0° C. The mixture was allowed to stir at 0° C. for 3 hours and was then allowed to warm to room temperature for 14 hours. The mixture was concentrated under reduced pressure and then purified by column chromatography on silica to afford (R)-tert-butyl (4-diazo-3-oxobutan-2-yl)carbamate. 1H NMR (500 MHz, DMSO-d6) δ 7.27 (d, J=7.4 Hz, 1H), 6.01 (s, 1H), 3.97-3.87 (m, 1H), 1.37 (s, 9H), 1.13 (d, J=7.3 Hz, 3H).

Provenance & Evidence