Sulfuric Acid → HCID 10691034, compound

HRID 1736156Notes

Reaction equation

HRID 1736156 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:30]([F:31])=[C:29]([NH:32]C(=O)C(C)(C)C)[C:9]2[C:10](=[O:28])[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH:20]C(=O)C(C)(C)C)=[C:16]([F:27])[CH:15]=3)[O:13][C:8]=2[C:7]=1[F:39])=[O:5])[CH3:2].S(=O)(=O)(O)O>>[NH2:32][C:29]1[C:9]2[C:10](=[O:28])[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([F:27])[CH:15]=3)[O:13][C:8]=2[C:7]([F:39])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:30]=1[F:31]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 10578490HCID 10578490, compound

Product 1

HCID 10691034HCID 10691034, compoundYield 50%

Procedure

740 mg (1.36 mol) of the above 7-ethoxycarbonyl-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one was subjected to the depivaloylation with concentrated sulfuric acid substantially in the same manner as that in Example 87 (2). The resulting solution was adjusted to pH 7 and extracted once with ethyl acetate. The organic layer was washed once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform) and recrystallized from ethyl acetate/n-hexane to give 259 mg of Compound 92 (yield: 50%) .

Workup

  1. extractionextracted once with ethyl acetate
  2. washThe organic layer was washed once with an aqueous saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform)
  6. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-59e4e64f7ce64cfeb436cc5a056e1d48
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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