Water → HCID 86647195, compound

HRID 1038550Notes

Reaction equation

HRID 1038550 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([CH2:23][CH2:24][CH3:25])=[CH:16][C:17]([C:20]([OH:22])=[O:21])=[N:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:26][C:27]1[C:32](O)=[C:31]([F:34])[C:30]([F:35])=[C:29]([F:36])[C:28]=1[F:37].C1(N=C=NC2CCCCC2)CCCCC1.O>C(OCC)(=O)C>[F:26][C:27]1[C:28]([F:37])=[C:29]([F:36])[C:30]([F:35])=[C:31]([F:34])[C:32]=1[O:21][C:20]([C:17]1[N:18]=[CH:19][C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]2)=[C:15]([CH2:23][CH2:24][CH3:25])[CH:16]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 66598276HCID 66598276, compound

Product 1

HCID 86647195HCID 86647195, compoundYield 119.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-4-propyl picolinic acid (134 mg, 0.307 mmol) was dissolved in ethyl acetate (6.2 mL). At room temperature, pentafluorophenol (68 mg, 0.368 mmol) and N,N′-dicyclohexylcarbodiimide (76 mg, 0.368 mmol) were added sequentially, and the mixture was stirred at room temperature overnight. The reaction solution was added water under ice-cold conditions, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (189 mg (yield >99%)) was obtained as a yellow brown crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4d3974e3fc634282b6273f42137bd870
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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