Sodium Hydroxide → (4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-5-fluoro-biphenyl-3-yl)-acetic Acid

HRID 547030Notes

Reaction equation

HRID 547030 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:40])[CH2:6][C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH2:38][CH3:39])([C:23]3[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([CH2:35][CH3:36])([OH:34])[CH2:32][CH3:33])=[C:25]([CH3:37])[CH:24]=3)[CH2:21][CH3:22])=[CH:16][CH:15]=2)[CH:10]=[C:11]([F:13])[CH:12]=1.[Cl-].[NH4+]>CO.O1CCCC1>[CH2:21]([C:20]([C:17]1[CH:16]=[CH:15][C:14]([C:9]2[CH:10]=[C:11]([F:13])[CH:12]=[C:7]([CH2:6][C:5]([OH:40])=[O:4])[CH:8]=2)=[CH:19][CH:18]=1)([C:23]1[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([CH2:32][CH3:33])([OH:34])[CH2:35][CH3:36])=[C:25]([CH3:37])[CH:24]=1)[CH2:38][CH3:39])[CH3:22]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57709075(4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-5-fluoro-biphenyl-3-yl)-acetic Acid Methyl Ester

Product 1

HCID 57709139(4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-5-fluoro-biphenyl-3-yl)-acetic AcidYield 68.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 1 N sodium hydroxide aqueous solution (0.335 mL, 0.335 mmol) was added to a solution of (4′-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-5-fluoro-biphenyl-3-yl)-acetic acid methyl ester (Example 127-(2); 57.7 mg, 0.112 mmol) in methanol-tetrahydrofuran (1:1, 4 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform:methanol=10:1) to give the target compound as a colorless oil (38.5 mg, 68%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-c15a6fbae8b34caaa7162be85b2dcfb4
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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