Potassium Carbonate → HCID 59715052, compound

HRID 2223901Notes

Reaction equation

HRID 2223901 reaction equation
C([O:4][CH2:5][C:6]([CH2:18][CH2:19][C:20]1([CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([N:34]([C:42]3[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=3)[C:35]([C:37]3[O:38][CH:39]=[CH:40][CH:41]=3)=[O:36])[CH2:30][CH2:29]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)([CH2:12][CH2:13][O:14]C(=O)C)[CH2:7][O:8]C(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:14][CH2:13][CH2:12][C:6]([CH2:5][OH:4])([CH2:7][OH:8])[CH2:18][CH2:19][C:20]1([CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH:31]([N:34]([C:42]3[CH:43]=[CH:44][C:45]([CH3:48])=[CH:46][CH:47]=3)[C:35]([C:37]3[O:38][CH:39]=[CH:40][CH:41]=3)=[O:36])[CH2:32][CH2:33]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59715054HCID 59715054, compound

Product 1

HCID 59715052HCID 59715052, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(acetoxymethyl)-2-[2-[1-[2-[4-[N-(p-tolyl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]ethyl]-1,4-diacetoxybutane (synthesized in Example 14) (313 mg) dissolved in methanol (5 mL) was added potassium carbonate (39 mg) at room temperature. The solution was stirred for 20 hours. The reaction solution was concentrated under reduced pressure. Water was added to the resulting residue and extracted with a mixed solvent of chloroform-ethanol (80:20). The organic layer was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure to give the title compound (252 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionWater was added to the resulting residue
  3. extractionextracted with a mixed solvent of chloroform-ethanol (80:20)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53bd46a6034a4e6098bf53334942613d
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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