Hydrochloric Acid → HCID 58181233, compound

Temperature

107.5 °C

To {4-[2-(2-acetylamino-1,3-thiazol-4-yl)ethyl]phenyl}acetic acid (6.00 g, 19.7 mmol) that was synthesized from N-(4-formyl-1,3-thiazol-2-yl)acetamide by Wittig reaction and hydrogenation reaction based on the method described in WO2006/28269 were added acetic acid (18 ml) and concentrated hydrochloric acid (24 ml), and the mixture was heated at 105-110° C. for 5 hrs. After cooling, the reaction mixture was concentrated to dryness. 5% Hydrogen chloride methanol solution (30 ml) was added to the residue, and the mixture was stirred at 40° C. for 1.5 hrs and at room temperature for 12 hrs. The reaction mixture was concentrated, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Diisopropyl ether was added to the residue, and the precipitate was collected by filtration, washed with diisopropyl ether and dried under reduced pressure to give methyl{4-[2-(2-amino-1,3-thiazol-4-yl)ethyl]phenyl}acetate (5.36 g, yield 98%) as a white solid.

1. temperatureAfter cooling
2. concentrationthe reaction mixture was concentrated to dryness
3. addition5% Hydrogen chloride methanol solution (30 ml) was added to the residue
4. concentrationThe reaction mixture was concentrated
5. additionsaturated aqueous sodium hydrogen carbonate solution was added
6. extractionthe mixture was extracted with ethyl acetate
7. washThe combined organic layer was washed with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. additionDiisopropyl ether was added to the residue
11. filtrationthe precipitate was collected by filtration
12. washwashed with diisopropyl ether
13. customdried under reduced pressure

ORD record

ord-de4c8a1404934e92bb2cdd9ad8ff827f

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999989B2