Trifluoroacetic acid → HCID 44159730, compound

Temperature

0 °C

To a solution of 2-(4{[2-(acetylamino)-1,3-thiazol-4-yl]methoxy}phenyl)ethyl tert-butyl hydrazine-1,2-dicarboxylate (0.855 mmol) in dichloromethane (30 ml) was added trifluoroacetic acid (3.18 ml, 42.8 mmol) at 0° C. After stirring at 0° C. for 30 min, the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted 4 times with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Ethyl acetate (20 ml) was added to suspend the residue. The suspension was filtered and washed once with ethyl acetate and 5 times with diethyl ether, and dried under reduced pressure to give the title compound (105.9 mg, 0.302 mmol, yield 35.3%) as a white solid.

1. stirringthe mixture was stirred at room temperature for 1 hr
2. concentrationThe reaction mixture was concentrated
3. additionaqueous sodium hydrogen carbonate solution was added to the residue
4. extractionthe mixture was extracted 4 times with ethyl acetate
5. washThe combined organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. additionEthyl acetate (20 ml) was added
9. filtrationThe suspension was filtered
10. washwashed once with ethyl acetate and 5 times with diethyl ether
11. customdried under reduced pressure

ORD record

ord-1e0c2ef678754727b1c6da10f17faa5c

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507690B2