Water → {5-[4-(1-ethyl-1-{4-[2-(1-hydroxy-cyclopentyl)-ethyl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-pyridin-3-yl}-acetic Acid Methyl Ester

HRID 547005Notes

Reaction equation

HRID 547005 reaction equation
[CH3:1][O:2][C:3](=[O:42])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH2:39][CH3:40])([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]4([O:33][Si](C)(C)C)[CH2:32][CH2:31][CH2:30][CH2:29]4)=[C:22]([CH3:38])[CH:21]=3)[CH2:18][CH3:19])=[CH:13][C:12]=2[CH3:41])[CH:10]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].O>O1CCCC1>[CH3:1][O:2][C:3](=[O:42])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH2:18][CH3:19])([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]4([OH:33])[CH2:29][CH2:30][CH2:31][CH2:32]4)=[C:22]([CH3:38])[CH:21]=3)[CH2:39][CH3:40])=[CH:13][C:12]=2[CH3:41])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 57709005{5-[4-(1-ethyl-1-{3-methyl-4-[2-(1-trimethylsilanyloxy-cyclopentyl)-ethyl]-phenyl}-propyl)-2-methyl-phenyl]-pyridin-3-yl}-acetic Acid Methyl Ester

Product 1

HCID 57443513{5-[4-(1-ethyl-1-{4-[2-(1-hydroxy-cyclopentyl)-ethyl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-pyridin-3-yl}-acetic Acid Methyl EsterYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{5-[4-(1-Ethyl-1-{3-methyl-4-[2-(1-trimethylsilanyloxy-cyclopentyl)-ethyl]-phenyl}-propyl)-2-methyl-phenyl]-pyridin-3-yl}-acetic acid methyl ester (Example 114-(1); 26.8 mg, 0.046 mmol) was dissolved in tetrahydrofuran (0.4 mL). Tetra-n-butylammonium fluoride (1 M solution in tetrahydrofuran; 0.05 mL, 0.05 mmol) was added at room temperature, and the mixture was stirred for two hours. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then, the resulting residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=3/1) to give the title compound (16.4 mg, 70%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThen, the resulting residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-248749e1223747a29623e82dd7eb208b
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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