Acetic Acid → HCID 59714986, compound

HRID 2223885Notes

Reaction equation

HRID 2223885 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][C:31]([NH:33][CH2:34][C:35]([O:37]CC)=[O:36])=[O:32])[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+].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][C:31]([NH:33][CH2:34][C:35]([OH:37])=[O:36])=[O:32])[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

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 59714896HCID 59714896, compound

Product 1

HCID 59714986HCID 59714986, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl [2-[1-[2-[4-[N-(5-methylpyridin-2-yl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetamido]acetate (221 mg) was dissolved in methanol (5 mL). A 2N aqueous sodium hydroxide solution (2.1 mL) was added to the solution, and it was stirred at room temperature for 16 hours. The solution was neutralized by addition of acetic acid (0.25 mL) (to pH of about 6). The solvent was distilled off under reduced pressure, and the resulting residue was extracted with 20% ethanol/chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give the title compound (170 mg).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionthe resulting residue was extracted with 20% ethanol/chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c4510d2ffdc0476391cf0d4c828d96c9
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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