Trifluoromethanesulfonic acid → HCID 20693366, compound

HRID 380074Notes

Reaction equation

HRID 380074 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH:7]([CH3:17])[CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[F:24][C:25]([F:31])([F:30])[S:26](O)(=[O:28])=[O:27]>ClCCl.N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:18])[CH:7]([CH3:17])[CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][S:26]([C:25]([F:31])([F:30])[F:24])(=[O:28])=[O:27])=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 20693379HCID 20693379, compound

Product 1

HCID 20693366HCID 20693366, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon and at −78° C., to a solution of the compound prepared in Example 1(2) (1.50 g) in dichioromethane (10 ml), pyridine (1.1 3 ml) and anhydrous trifluoromethanesulfonic acid (1.13 ml) were added dropwise. The mixture solution was stirred for 2 hours at room temperature. A saturated aqueous solution of sodium bicarbonate (20 ml) was added to the reaction mixture and it was vigorously stirred for 1 hour at room temperature. The reaction mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (hexane:ethyl acetate=19: 1) to give the title compound (2.05 g) having the following physical data.

Workup

  1. stirringwas vigorously stirred for 1 hour at room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (hexane:ethyl acetate=19: 1)

Sources & evidence

ORD record
ord-fe6428d3c26244069302111fcaf6d176
Source dataset
uspto-grants-2001_10
Patent number
US06300514B1

Reaction notes

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