Acetic Anhydride → HCID 44250878, compound

HRID 1619157Notes

Reaction equation

HRID 1619157 reaction equation
[OH:1]/[N:2]=[C:3](/[NH2:25])\[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]4([CH2:24][CH2:23][CH2:22][CH2:21]4)[C:16](=[O:20])[NH:17]3)=[CH:13][CH:12]=2)[CH:5]=1.[C:26](OC(=O)C)(=O)[CH3:27]>>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]2[N:25]=[C:26]([CH3:27])[O:1][N:2]=2)=[CH:5][C:6]=1[C:11]1[CH:19]=[C:18]2[C:14]([C:15]3([CH2:21][CH2:22][CH2:23][CH2:24]3)[C:16](=[O:20])[NH:17]2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 87332000HCID 87332000, compound

Product 1

HCID 44250878HCID 44250878, compoundYield 32%

Conditions

Temperature
130 °C

Procedure

A mixture of (E)-N′-hydroxy-4-methyl-3-(2′-oxospiro[cyclopentane-1,3′-indoline]-6′-yl)benzimidamide (preparation 54, 31 mg, 0.09 mmol) and acetic anhydride (0.03 mL, 0.28 mmol) was heated in a sealed tube 130° C. for 1 h. The solvent was concentrated under reduced pressure and the residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate solution, brine, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography (8:2 hexanes/ethyl acetate to ethyl acetate) to yield the title compound (0.01 g, 32%) as a white solid.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate solution, brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was purified by flash chromatography (8:2 hexanes/ethyl acetate to ethyl acetate)

Sources & evidence

ORD record
ord-660e623a0211494085a7d9607309a042
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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