Trifluoroacetic acid → HCID 59396710, compound

HRID 1696711Notes

Reaction equation

HRID 1696711 reaction equation
COC1C=CC(C[O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]([OH:29])[C@@H:16]([S:18][C:19]3[C:24](OCOC)=[CH:23][CH:22]=[CH:21][N:20]=3)[CH3:17])=[CH:11][CH:10]=2)=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>>[CH3:17][C@H:16]1[C@H:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[O:29][C:24]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[S:18]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 68710690HCID 68710690, compound

Product 1

HCID 59396710HCID 59396710, compound

Procedure

The compound synthesized in the above (6) was mixed with anisole (8.52 mL, 78.8 mmol) and trifluoroacetic acid (20 mL, 0.26 mol) under cooling with ice, and stirred for 15 minutes under cooling with ice. Aqueous saturated sodium hydrogencarbonate solution was added, then the reaction solution was extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium hydrogencarbonate solution, water and saturated saline in that order, and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel flash column chromatography (hexane/ethyl acetate=1/1), and further recrystallized (ethyl acetate/n-heptane) to obtain the entitled compound (1.9 g, 35% in 2 steps) as a white solid.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous saturated sodium hydrogencarbonate solution, water and saturated saline in that order
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel flash column chromatography (hexane/ethyl acetate=1/1)
  8. customfurther recrystallized (ethyl acetate/n-heptane)
  9. customto obtain the entitled compound (1.9 g, 35% in 2 steps) as a white solid

Sources & evidence

ORD record
ord-1fd8207225294522a17291319f16549d
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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