Methyl iodide → HCID 51356285, compound

Participants

Reaction Conditions

Reaction Steps

Into a 250 mL RB flask was added dimethyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-D-glutamate (4 g, 14.53 mmol) and cool in Dry Ice/Aceton −78° C. bath. By cannulation was added by drop wise 1M LiHMDS in THF (30.5 mL, 30.5 mmol. After addition the mixture was let stir at −78° C. for 0.5 hours. Then methyl iodide (1.817 mL, 29.1 mmol) was added as rapidly as possible, and the solution was stirred at −78° C. for 4.5 hours. The reaction was then quenched with 1N HCl solution (40 mL), and extracted with EtOAc (3×50 mL). The organics were combined and washed with saturated NaHCO3, brine, then dried over Na2SO4 and concentrated to give a red amber color oil. The oil was then purified on a Biotage SNAP 50 g column with a gradient of 0 to 35% gradient EtOAc in Hexane over 35 minutes. The fractions with product were combined to isolate the title compound (1.37 g) as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ 1.08 (d, J=7.1 Hz, 3H), 1.38 (s, 9H), 1.71 (ddd, J=13.6, 8.3, 5.1 Hz, 1H), 1.94 (ddd, J=13.9, 10.1, 6.1 Hz, 1H), 2.43-2.49 (m, 1H), 3.60 (s, 3H), 3.62 (s, 3H), 4.01 (ddd, J=9.9, 8.4, 5.2 Hz, 1H), 7.29 (d, J=8.3 Hz, 1H).

Provenance & Evidence