Sodium Hydroxide → HCID 57708946, compound

HRID 546820Notes

Reaction equation

HRID 546820 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:48])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH:33]([O:38][Si](C(C)(C)C)(C)C)[C:34]([CH3:37])([CH3:36])[CH3:35])=[C:27]([CH3:46])[CH:26]=3)([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:16][C:15]=2[CH3:47])=[CH:10][CH:9]=1.P([O-])(O)(O)=O.[Na+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.CO>[CH2:21]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][C:5]([OH:48])=[O:4])=[CH:13][CH:12]=2)=[C:15]([CH3:47])[CH:16]=1)([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH:33]([OH:38])[C:34]([CH3:36])([CH3:37])[CH3:35])=[C:27]([CH3:46])[CH:26]=1)[CH2:23][CH3:24])[CH3:22]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 23672064Monosodium phosphate2×HCID 57709126HCID 57709126, compound

Product 1

HCID 57708946HCID 57708946, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A sodium hydroxide aqueous solution (1 M, 0.5 mL, 0.5 mmol) was added to a mixture of 3-[4′-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2′-methyl-biphenyl-4-yl]-propionic acid methyl ester (Example 11-(3); 0.013 g, 0.02 mmol), tetrahydrofuran (0.5 mL) and methanol (1.0 mL) while stirring at room temperature, and the mixture was stirred at the same temperature for two hours. A 30% sodium dihydrogenphosphate aqueous solution was 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. Tetra-n-butylammonium fluoride (1 M solution in tetrahydrofuran, 0.1 mL, 0.1 mmol) and tetrahydrofuran (1 mL) were added to the resulting residue, and the mixture was stirred at 60° C. for four hours. A 30% sodium dihydrogenphosphate aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a 30% sodium dihydrogenphosphate aqueous solution and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (dichloromethane/methanol=10/1) to give the title compound (0.007 g, 67%).

Workup

  1. stirringthe mixture was stirred at the same temperature for two hours
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. stirringthe mixture was stirred at 60° C. for four hours
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with a 30% sodium dihydrogenphosphate aqueous solution and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by preparative TLC (dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-c64ec069a6da43e48f11757d80c1f8e1
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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