Sodium Hydroxide → (3-chloro-4'-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2'-methyl-biphenyl-4-yl)-acetic Acid

HRID 546939Notes

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[Cl:44]>CO.O1CCCC1>[Cl:44][C:8]1[CH:9]=[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:31]([F:32])([F:33])[F:34])[C:35]([F:37])([F:38])[F:36])=[C:24]([CH3:40])[CH:23]=3)[CH2:20][CH3:21])=[CH:15][C:14]=2[CH3:43])[CH:11]=[CH:12][C:7]=1[CH2:6][C:5]([OH:45])=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A 1 N sodium hydroxide aqueous solution (0.019 mL, 0.019 mmol) was added to a solution of (3-chloro-4′-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2′-methyl-biphenyl-4-yl)acetic acid methyl ester (Example 73-(1); 3.9 mg, 0.006 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 (2.0 mg, 53%).

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-446c4f215bb34631a4b49172dc893fb0
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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