HCID 13082363, compound → HCID 19029215, compound

Participants

Reaction Conditions

Reaction Steps

Vinyl magnesium bromide (10.9 mL, 1N, 10.9 mmol) was slowly added to a cooled (-78° C.) solution of ethyl 2-acetamido-2-bromoacetate (1.10 g, 4.91 mmol) in THF (50 mL). The reaction was stirred at -78° C. (2 h), and was then quenched with a 1N citric acid solution (7.0 mL). The mixture was allowed to warm to room temperature, and then the THF was removed in vacuo. The aqueous mixture was extracted with CHCl3 (3×100 mL), and the combined CHCl3 extracts were dried (Na2SO4) and concentrated to dryness. The residue was purified by flash chromatography using SiO2 gel and 2% MeOH/CHCl3 as the eluant to give 0.50 g (60%) of the desired product as a light yellow colored oil: Rf 0.51 (4% MeOH/CHCl3); 1H NMR (DMSO-d6) δ 1.17 (t, J=7.1 Hz, OCH2CH3), 1.88 (s, C(O)CH3), 4.09 (d, J=7.1 Hz, OCH2CH3), 4.80-4.86 (m, α-CH), 5.22-5.35 (m, CH=CH2), 5.82-5.92 (m, CH=CH2), 8.47 (d, J=7.4 Hz, NH); 13C NMR (DMSO-d6) 13.96 (OCH2CH3), 22.12 (C(O)CH3), 54.65 (α-CH), 60.71 (OCH2CH3), 117.89 (CH=CH2), 132.48 (CH=CH2), 169.16 (C(O)CH3), 170.26 (C(O)NH) ppm.

Provenance & Evidence