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

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.

1. customA mild exothermic reaction
2. customresulted
3. temperatureThe brown mixture was heated
4. temperatureto reflux
5. stirringstirred overnight
6. concentrationthe mixture was concentrated to a volume of 400 mL
7. additionpoured into Et2O (1500 mL)
8. customThe precipitated white solid was collected
9. customdried in vacuo

ORD record

ord-d4145b5c17b54f0da5edaea2dfd64f1a

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05874472