Acetic Acid → HCID 59714993, compound

HRID 2223887Notes

Reaction equation

HRID 2223887 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3([CH2:30][CH2:31][CH2:32][C:33]([O:35]C)=[O:34])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:18][CH2:17]2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[N:6][CH:7]=1.[OH-].[Na+].O.C(O)(=O)C>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3([CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:18][CH2:17]2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 10278391HCID 10278391, compound

Product 1

HCID 59714993HCID 59714993, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-[1-[2-[4-[N-(5-methylpyridin-2-yl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]butyrate (210 mg) in methanol (10 mL) was added a 3N aqueous sodium hydroxide solution (1.4 mL) at room temperature. After stirring the solution at room temperature for 3 hours, a 3N aqueous sodium hydroxide solution (0.7 mL) was added thereto at room temperature. The solution was stirred at room temperature for 2 hours. Water (5 mL) and acetic acid (0.36 mL) were then added to the solution and it was concentrated under reduced pressure to distill off the methanol. The solution was extracted with 20% ethanol/chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (180 mg).

Workup

  1. customat room temperature
  2. stirringThe solution was stirred at room temperature for 2 hours
  3. concentrationwas concentrated under reduced pressure
  4. distillationto distill off the methanol
  5. extractionThe solution was extracted with 20% ethanol/chloroform
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b54c10f0082b4b549baf84c928ee0fbb
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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