Acetic Acid → HCID 21979852, compound

HRID 10536Notes

Reaction equation

HRID 10536 reaction equation
[CH3:1][S:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:6]=[N:5][CH:4]=1.C(O)(=[O:29])C.OO>C(OCC)(=O)C>[CH3:1][S:2]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]2)[CH:6]=[N:5][CH:4]=1)=[O:29]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 21979971HCID 21979971, compound

Product 1

HCID 21979852HCID 21979852, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Intermediate 74 (746 mg) obtained in Example 105, Step B was added with acetic acid (1.5 ml) and 30% aqueous hydrogen peroxide (2 ml) and stirred at room temperature for 17 hours. The reaction mixture was added with ethyl acetate (50 ml) and washed three times with saturated aqueous sodium hydrogencarbonate (25 ml for each time), and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:acetone=3:1) to obtain the title compound (390 mg).

Workup

  1. washwashed three times with saturated aqueous sodium hydrogencarbonate (25 ml for each time), and the organic layer
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (n-hexane:acetone=3:1)

Sources & evidence

ORD record
ord-43fad62811f54559b279903164b86c04
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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