Methanol → HCID 14732250, compound

Participants

Reaction Steps

Step G (1): Thionyl chloride (1.7 g, 14.4 mmol) was added to a round bottom flask charged with a solution of (S)-2-(tert-butoxycarbonyl(methyl)-amino)pent-4-enoic acid (1.66 g, 7.2 mmol) [Tetrahedron (1991), 47(29), pp. 5453-62] in MeOH at 0° C. After complete addition, the reaction mixture was heated at reflux for 2 h, then cooled to rt. The resulting solution was concentrated in vacuo and the residual volatiles were removed on high vacuum overnight to afford 1.32 g (quantitative yield) of the title compound as an off-white solid. LC-MS (M+H)+=143.96; [α]D +3.7 (c=7.57 mg/mL, methanol); 1H NMR (500 MHz, CD3OD) δ ppm 2.71-2.84 (m, 5H) 3.88 (s, 2H) 4.19 (t, J=5.65 Hz, 1H) 4.84 (s, 2H) 5.26-5.38 (m, 1H) 5.68-5.83 (m, 1H).

Provenance & Evidence