Hydrochloric Acid → 3-{2-Fluoro-4-[(4-{1-[(4-phenyl-1,3-thiazol-2-yl)thio]butyl}benzyl)oxy]phenyl}propanoic acid

HRID 732203Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 3-{2-fluoro-4-[(4-{1-[(4-phenyl-1,3-thiazol-2-yl)thio]butyl}benzyl)oxy]phenyl}propanoate (0.130 g, 0.236 mmol) in a mixture of ethanol (0.5 mL) and tetrahydrofuran (1 mL) was added 2N aqueous sodium hydroxide solution (0.25 mL) and the mixture was stirred at 50° C. for 3 hr. Water was added to the reaction mixture, and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-70:30) to give the title compound (0.119 g, yield 97%) as a colorless oil.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-70:30)

Sources & evidence

ORD record: ord-db09b5093de84474a3dd7cd5ff67e65e
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585880B2

Reaction notes

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