Water → HCID 86647182, compound

HRID 1038523Notes

Reaction equation

HRID 1038523 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=2/[CH:26]=[CH:27]\[CH3:28])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]1[C:35](O)=[C:34]([F:37])[C:33]([F:38])=[C:32]([F:39])[C:31]=1[F:40].C1(N=C=NC2CCCCC2)CCCCC1.O>C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([O:23][C:35]3[C:34]([F:37])=[C:33]([F:38])[C:32]([F:39])=[C:31]([F:40])[C:30]=3[F:29])=[O:22])=[CH:19][C:18]=2/[CH:26]=[CH:27]\[CH3:28])[CH2:15][CH2:16]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 66598328HCID 66598328, compound

Product 1

HCID 86647182HCID 86647182, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(Z)-4-{4-[2-(benzyloxy)ethyl]piperazin-1-yl}-3-(prop-1-en-1-yl)benzoic acid (13 mg, 0.0331 mmol) was dissolved in ethyl acetate (3.3 mL). At room temperature, pentafluorophenol (7.3 mg, 0.0397 mmol) and N,N′-dicyclohexylcarbodiimide (8.2 mg, 0.0397 mmol) were added sequentially, and the mixture was stirred at room temperature for 14 hours. The reaction solution was added water, 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/acetone). The title compound (16 mg (yield 86%)) was obtained as a pale yellow 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/acetone)

Sources & evidence

ORD record
ord-82ff3c923f5049dba463561925917d39
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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