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

HRID 1095961Notes

Reaction equation

C([O:3][C:4](=[O:38])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:36])[C:20]([OH:35])([C:25]3[CH:26]=[N:27][C:28]4[C:33]([CH:34]=3)=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:21]([F:24])([F:23])[F:22])=[C:15]([Cl:37])[CH:14]=2)=[CH:7][CH:6]=1)C.[Li+].[OH-].Cl.O>O1CCCC1.C(O)C>[Cl:37][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[CH:19]([CH3:36])[C:20]([OH:35])([C:25]1[CH:26]=[N:27][C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:21]([F:24])([F:23])[F:22])[O:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:38])=[O:3])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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+].

Workup

stirringthe mixture was stirred overnight at room temperature
temperatureThe mixture was cooled in an ice bath
customa precipitation
customwas formed
filtrationThe suspension was filtered
washthe solid was washed with diethyl ether
customdried

Sources & evidence

ORD record: ord-cf95f4b640914742a62f9d63864da7d6
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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