Acetic Anhydride → HCID 22272789, compound

HRID 1064814Notes

Reaction equation

HRID 1064814 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]([NH:29][C:30]2[C:35]([CH:36]([CH3:38])[CH3:37])=CC(O)=[CH:32][C:31]=2[CH:40]([CH3:42])[CH3:41])=[O:28])[CH2:22][CH2:21]1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][N:23]([CH2:26][C:27]([NH:29][C:30]2[C:35]([CH:36]([CH3:37])[CH3:38])=[CH:6][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:32][C:31]=2[CH:40]([CH3:42])[CH3:41])=[O:28])[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 22272702HCID 22272702, compound

Product 1

HCID 22272789HCID 22272789, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (2 ml) was dropped into a solution of 2-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-4-hydroxyphenyl)acetamide (149 mg, 0.3 mmol) in pyridine (1 ml) with ice cooling and the mixture was stirred at room temperature for 3 hours. The reaction solution was neutralized by adding a saturated aqueous solution of sodium bicarbonate thereto and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=20:1) to provide 166 mg (yield 100%) of the desired compound as colorless needles.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution successively and dried over sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-fdcbe8108f034474a8b2019aad892ab5
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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