Hydrochloric Acid → 4-[3-Chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenoxymethyl]-benzoic acid

Temperature

0 °C

To a solution of 4-[3-chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenoxymethyl]-benzoic acid ethyl ester (Example 140, 30 mg) in tetrahydrofuran (1 ml) and ethanol (1 ml) was added a 1 M aqueous LiOH solution (0.3 ml) at 0° C. The mixture was stirred at 0° C. for 2 h. More LiOH solution (0.23 ml) was added and the mixture was stirred overnight at room temperature. The mixture was cooled in an ice bath and acidified using 1 M aqueous HCl. After addition of water a precipitation was formed. The suspension was filtered and the solid was washed with diethyl ether and dried to give the title compound as a colorless solid (19 mg). MS (m/e)=515.9 [M+H+].

1. stirringthe mixture was stirred overnight at room temperature
2. temperatureThe mixture was cooled in an ice bath
3. customa precipitation
4. customwas formed
5. filtrationThe suspension was filtered
6. washthe solid was washed with diethyl ether
7. customdried

ORD record

ord-cf95f4b640914742a62f9d63864da7d6

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138189B2