Water → Acetamidophenyl methoxypropionic acid

Temperature

90 °C

To (R)-(−)-3-(4-aminophenyl)-2-methoxypropionic acid (40 g) in a 0.5 L glass reactor was added ethyl acetate (80 g) and acetic anhydride (62.8 g). The mixture was stirred at 90° C. for 1 hour. Upon cooling, the solvent was removed by vacuum distillation, providing an oily residue. To this residue was added water (120 g) and ethyl acetate (120 g). After stirring for 10 min at 35° C., the layers were separated and the aqueous layer discarded. The organic layer solvent was removed by vacuum distillation. Acetone (120 g) was then added and the resulting mixture was warmed until dissolution was complete. The solution was cooled to 0° C., and the product precipitated which was collected by filtration. The solid was rinsed with acetone (20 g) and dried at 65° C. to afford 26 g of the title compound.

1. temperatureUpon cooling
2. customthe solvent was removed by vacuum distillation
3. customproviding an oily residue
4. stirringAfter stirring for 10 min at 35° C.
5. customthe layers were separated
6. customThe organic layer solvent was removed by vacuum distillation
7. additionAcetone (120 g) was then added
8. temperaturethe resulting mixture was warmed until dissolution
9. temperatureThe solution was cooled to 0° C.
10. customthe product precipitated which
11. filtrationwas collected by filtration
12. washThe solid was rinsed with acetone (20 g)
13. customdried at 65° C.

ORD record

ord-332227b3343d4d5d94cb686f1c5abfa9

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754127B2