Ethyl chloroformate → HCID 67027247, compound

Participants

Reaction Steps

To a solution of Compound 1046 (3.36 g, 15.75 mmol) in ethanol (100 mL) was added saturated sodium bicarbonate (25 mL) and ethyl chloroformate (1.801 mL, 18.9 mmol). The reaction mixture was stirred at room temperature overnight, at which point 1.0 M aqueous potassium hydroxide (63.0 mL, 63.0 mmol) was added. The mixture was stirred at room temperature overnight, concentrated under reduced pressure, made acidic with 6N HCl, and extracted with 10% nBuOH in chloroform. The organics were concentrated to give 3-(ethoxycarbonyl(thiophen-3-ylmethyl)amino)propanoic acid as a tan oil (Compound 1048, 2.04 g, 50%); 1H NMR (300 MHz, CDCl3): δ 7.56-7.48 (m, 1H), 7.44-7.38 (m, 2H), 4.75 (s, 2H), 4.49-4.39 (m, 4H), 3.92-3.77 (m, 2H), 2.62-2.58 (m, 2H) and 1.68-1.48 (m, 3H).

Provenance & Evidence