Sodium Hydroxide → HCID 57709097, compound

HRID 547011Notes

Reaction equation

HRID 547011 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:42])[CH2:7][C:8]1[CH:9]=[N:10][C:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([C:21]([CH2:39][CH3:40])([C:24]3[CH:29]=[CH:28][C:27](/[CH:30]=[CH:31]/[C:32]([CH2:36][CH3:37])([OH:35])[CH2:33][CH3:34])=[C:26]([CH3:38])[CH:25]=3)[CH2:22][CH3:23])=[CH:16][C:15]=2[CH3:41])=[CH:12][CH:13]=1)C.[Cl-].[NH4+]>CO.O1CCCC1>[CH2:22]([C:21]([C:17]1[CH:18]=[C:19]([CH3:20])[C:14]([C:11]2[N:10]=[CH:9][C:8]([CH2:7][C:6]([OH:42])=[O:5])=[CH:13][CH:12]=2)=[C:15]([CH3:41])[CH:16]=1)([C:24]1[CH:29]=[CH:28][C:27](/[CH:30]=[CH:31]/[C:32]([CH2:33][CH3:34])([OH:35])[CH2:36][CH3:37])=[C:26]([CH3:38])[CH:25]=1)[CH2:39][CH3:40])[CH3:23]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57709057HCID 57709057, compound

Product 1

HCID 57709097HCID 57709097, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 1 N sodium hydroxide aqueous solution (0.063 mL, 0.063 mmol) was added to a solution of (E)-[6-(4-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2,6-dimethyl-phenyl)-3-pyridinyl]-acetic acid ethyl ester (Example 119-(1); 11.6 mg, 0.021 mmol) in methanol-tetrahydrofuran (1:1, 2 mL), and the mixture was stirred at room temperature for six 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 (chloroform:methanol=10:1) to give the target compound as a colorless oil (6.4 mg, 59%).

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-4e5fe5e710fd43d08a5ef9b2a7e055d3
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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