Acetic Anhydride → HCID 86757744, compound

HRID 1251085Notes

Reaction equation

HRID 1251085 reaction equation
[F:1][C:2]1([F:38])[CH2:3][CH2:4][N:5]([C:24]([C:26]2[S:30][C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:28][C:27]=2[CH3:37])=[O:25])[C:6]2[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:12]1[CH2:17][CH2:16][C:15](=[N:18][OH:19])[CH2:14][CH2:13]1)=[O:11].[C:39](OC(=O)C)(=[O:41])[CH3:40]>N1C=CC=CC=1>[F:38][C:2]1([F:1])[CH2:3][CH2:4][N:5]([C:24]([C:26]2[S:30][C:29]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[N:28][C:27]=2[CH3:37])=[O:25])[C:6]2[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:12]1[CH2:13][CH2:14][C:15](=[N:18][O:19][C:39](=[O:41])[CH3:40])[CH2:16][CH2:17]1)=[O:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86757743HCID 86757743, compound

Product 1

HCID 86757744HCID 86757744, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 51 mg of (Z)-4,4-difluoro-5-{2-[4-(hydroxyimino)piperidino]-2-oxoethylidene}-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepine in a mixture of 800 μl of acetic anhydride and 800 μl of pyridine was stirred at room temperature for eight hours. The solvent was evaporated, the residue was dissolved in ethyl acetate, and the solution was washed with 1N hydrochloric acid and a saturated aqueous solution of NaCl. After drying over anhydrous magnesium sulfate, the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (eluting with chloroform) to give 36 mg of (Z)-4,4-difluoro-5-{2-[4-(acetoxyimino)piperidino]-2-oxoethylidene}-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepine as a colorless solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe solution was washed with 1N hydrochloric acid
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (eluting with chloroform)

Sources & evidence

ORD record
ord-ddbf4cc471dd4ac78fb977948a71289c
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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