Methanol → sodium (4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)-acetate

HRID 546892Notes

Reaction equation

HRID 546892 reaction equation
CO.[OH-].[Na+:4].[CH2:5]([C:7]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37][C:38]([O:40]C)=[O:39])=[C:33]([F:42])[CH:32]=2)=[C:27]([CH3:43])[CH:26]=1)([C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([CH2:22][CH3:23])([OH:21])[CH2:19][CH3:20])=[C:12]([CH3:24])[CH:11]=1)[CH2:8][CH3:9])[CH3:6].[Cl-].[NH4+]>O1CCCC1>[CH2:5]([C:7]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37][C:38]([O-:40])=[O:39])=[C:33]([F:42])[CH:32]=2)=[C:27]([CH3:43])[CH:26]=1)([C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([CH2:19][CH3:20])([OH:21])[CH2:22][CH3:23])=[C:12]([CH3:24])[CH:11]=1)[CH2:8][CH3:9])[CH3:6].[Na+:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57709052methyl (4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)-acetate

Product 1

HCID 23691963sodium (4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)-acetateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanol (1.3 mL), tetrahydrofuran (1.3 mL) and a 1 M sodium hydroxide aqueous solution (0.133 mL, 0.133 mmol) were added to methyl (4′-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-3-fluoro-2′-methyl-biphenyl-4-yl)acetate (23.5 mg, 0.044 mmol), and the mixture was stirred at room temperature for 18 hours. The reaction solution was poured into a saturated aqueous ammonium chloride solution, and then the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (chloroform/methanol=10/1). The purified product was diluted with methanol. After addition of sodium methoxide, the mixture was dried under reduced pressure to give the title compound (17.7 mg, 78%).

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative TLC (chloroform/methanol=10/1)
  5. additionThe purified product was diluted with methanol
  6. additionAfter addition of sodium methoxide
  7. customthe mixture was dried under reduced pressure

Sources & evidence

ORD record
ord-f394c3d060414b16ba1606857d4c71c3
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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