Acetyl chloride → Methyl 2-amino-2-(thiophen-2-yl)acetate

Participants

Reaction Steps

To dry MeOH (1000 mL) stirring at room temperature was added acetyl chloride (40.3 g, 513 mmol) over a 5 minute period. A mild exothermic reaction resulted. The mixture was stirred for 10 minutes and DL-α-amino-2-thiopheneacetic acid (40.5 g, 257 mmol) was added. The brown mixture was heated to reflux and stirred overnight. After cooling to room temperature, the mixture was concentrated to a volume of 400 mL and poured into Et2O (1500 mL). The precipitated white solid was collected and dried in vacuo to afford 49.2 g (92%) of the title compound as its hydrochloride salt. The 1H NMR spectrum was consistent for the title compound. An analytical sampie was recrystallized from EtOAc-hexane. Mpt.=182° C.

Provenance & Evidence