Sodium Hydroxide → [3-Fluoro-2'-Methyl-4'-(3-{3-Methyl-4-[(1e)-4,4,4-Trifluoro-3-Hydroxy-3-(Trifluoromethyl)but-1-En-1-Yl]phenyl}pentan-3-Yl)biphenyl-4-Yl]acetic Acid

HRID 546937Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5](=[O:45])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH2:41][CH3:42])([C:22]3[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([OH:39])([C:35]([F:38])([F:37])[F:36])[C:31]([F:34])([F:33])[F:32])=[C:24]([CH3:40])[CH:23]=3)[CH2:20][CH3:21])=[CH:15][C:14]=2[CH3:43])=[CH:9][C:8]=1[F:44]>CO.O1CCCC1>[CH2:20]([C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][C:5]([OH:45])=[O:4])=[C:8]([F:44])[CH:9]=2)=[C:14]([CH3:43])[CH:15]=1)([C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([OH:39])([C:35]([F:36])([F:37])[F:38])[C:31]([F:33])([F:34])[F:32])=[C:24]([CH3:40])[CH:23]=1)[CH2:41][CH3:42])[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

A 1 N sodium hydroxide aqueous solution (0.145 mL, 0.145 mmol) was added to a solution of (4′-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-3-fluoro-2′-methyl-biphenyl-4-yl)acetic acid methyl ester (Example 72-(1); 29.6 mg, 0.049 mmol) in methanol-tetrahydrofuran (1:1, 1 mL), and the mixture was stirred at 60° C. for one hour. Then, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform:methanol=8:3, saturated with water) to give the target compound as a colorless oil (27.5 mg, 95%).

Workup

concentrationThen, the reaction mixture was concentrated under reduced pressure
customThe resulting residue was purified by silica gel chromatography (chloroform:methanol=8:3, saturated with water)

Sources & evidence

ORD record: ord-36b9db374c484608b073bfa4903f48bd
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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