Acetic Acid → HCID 21931926, compound

HRID 500588Notes

Reaction equation

HRID 500588 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7](O)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10]C=2)=[CH:4][CH:3]=1.[C:17]([OH:20])(=O)C.OO.C(Cl)[Cl:24]>FC(F)(F)C(O)=O>[Cl:24][C:12]1[CH:11]=[CH:10][C:7]2[O:6][C:5]3[CH:15]=[CH:16][C:2]([CH2:17][OH:20])=[CH:3][C:4]=3[C:8]=2[CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 6344DichloromethaneHCID 54066592HCID 54066592, compound

Product 1

HCID 21931926HCID 21931926, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of Example 26 (6.4 g, 14 mmol) in methylenechloride (40 ml) and trifluoroacetic acid (20 ml) was stirred at RT for 0.5 h, then evaporated to dryness. The residue was dissolved in 100 ml water and 100 ml methylenechloride, then neutralized to pH 8 by 0.5 N NaOH, the organic phase was washed by water, dried over Na2SO4, evaporated to give the deprotected intermediate which was mixed with acetic acid (100 ml) and 30% H2O2 (2.5 ml). The mixture was stirred at RT for 2 hr, evaporated, purified by flash chromatography (methylenechloride/methanol, 15/1 saturated by 28% aqueous ammonia) and recrystallization in 50 ml ethyl acetate to give 4 g Example 45 as a white solid.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in 100 ml water
  3. washthe organic phase was washed by water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto give the deprotected intermediate which
  7. customevaporated
  8. custompurified by flash chromatography (methylenechloride/methanol, 15/1 saturated by 28% aqueous ammonia) and recrystallization in 50 ml ethyl acetate

Sources & evidence

ORD record
ord-0ae94fd35a9041128474b2dd39bb3c41
Source dataset
uspto-grants-2010_08
Patent number
US07772237B2

Reaction notes

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