Water → HCID 89962331, compound

HRID 338009Notes

Reaction equation

HRID 338009 reaction equation
C([O:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:12][C@@H:11]1[C:24]1[N:28]([CH3:29])[N:27]=[CH:26][CH:25]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CO>[Si:17]([O:16][C@H:13]1[CH2:14][CH2:15][C@H:10]([OH:9])[C@@H:11]([C:24]2[N:28]([CH3:29])[N:27]=[CH:26][CH:25]=2)[CH2:12]1)([C:20]([CH3:23])([CH3:21])[CH3:22])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 89963014HCID 89963014, compound

Product 1

HCID 89962331HCID 89962331, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the (1S*,2R*,4S*)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(1-methyl-1H-pyrazol-5-yl)cyclohexyl benzoate (367 mg, 0.885 mmol) prepared in Example 162e and potassium carbonate (245 mg, 1.77 mmol) in methanol (5.0 mL) was stirred at room temperature for 3 hours. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was washed twice with water (100 mL) and dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=3:2) to yield the title compound (187 mg, 68%) as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate (50 mL)
  2. washThe thus obtained organic layer was washed twice with water (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter vacuum concentration
  5. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=3:2)

Sources & evidence

ORD record
ord-6cbe1a84b5ee4757a80c15d89d462c3d
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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