Methyl 2-isocyanato-2-methylpropanoate → HCID 10276449, compound

Participants

Reaction Steps

A solution of Example 3G (19.7 g) in THF (100 mL) at room temperature was treated with the solution of the methyl 2-isocyanato-2-methylpropanoate in THF, stirred for 25 minutes, and concentrated to a volume of 170 mL. The concentrate was treated with THF (80 mL) and 6M HCl (95 mL), heated to reflux, stirred for 6 hours, cooled to room temperature, concentrated, and extracted with isopropyl acetate. The extract was washed sequentially with water, saturated NaHCO3, and brine, dried (Na2SO4), filtered, and concentrated to provide 24.2 g of the desired product. 1H NMR (300 MHz, DMSO-d6) δ8.33 (s, 1H), 7.47 (m, 2H), 7.35 (m, 5H), 6.90 (m, 2H), 6.78 (d, 1H, J=5 Hz), 4.65 (m, 2H), 4.00 (m, 2H), 3.68 (m, 1H), 3.55 (m, 2H), 1.30 (s, 3H), 1.28 (s, 3H).

Provenance & Evidence