Sodium Hydroxide → HCID 57709034, compound

HRID 547009Notes

Reaction equation

HRID 547009 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:42])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([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:15][C:14]=2[CH3:40])=[CH:9][C:8]=1[F:41].[Cl-].[NH4+]>CO.O1CCCC1>[CH2:21]([C:20]([C:16]1[CH:17]=[C:18]([CH3:19])[C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][C:5]([OH:42])=[O:4])=[C:8]([F:41])[CH:9]=2)=[C:14]([CH3:40])[CH:15]=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 57709182HCID 57709182, compound

Product 1

HCID 57709034HCID 57709034, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 1 N sodium hydroxide aqueous solution (0.180 mL, 0.180 mmol) was added to a solution of (E)-(4′-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-3-fluoro-2′,6′-dimethyl-biphenyl-4-yl)acetic acid methyl ester (Example 118-(1); 32.5 mg, 0.060 mmol) in methanol-tetrahydrofuran (1:1, 4 mL), and the mixture was stirred at room temperature for 10 hours. 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 (hexane:ethyl acetate=1:1) to give the target compound as a colorless oil (23.8 mg, 75%).

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 (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d8a1d259d0904b24a5fed4fd1078a388
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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