Trifluoroacetic acid → HCID 69736995, compound

HRID 25335Notes

Reaction equation

HRID 25335 reaction equation
FC(F)(F)C(O)=O.C1O[C:11]2([C:20]3[C:14]4[C:15](=[CH:21][N:22]([S:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)(=[O:26])=[O:25])[CH2:23][C:13]=4[CH2:12]2)[CH:16]=[CH:17][O:18][CH:19]=3)[O:10]C1>O>[C:27]1([S:24]([N:22]2[CH2:23][C:13]3[CH2:12][C:11](=[O:10])[C:20]4=[CH:19][O:18][CH:17]=[CH:16][C:15]([C:14]=34)=[CH:21]2)(=[O:26])=[O:25])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 865905872-Benzenesulfonyl-2,9-dihydro-6-oxa-2-azabenzo[cd]azulen-8-one Ethylene Ketal

Product 1

HCID 69736995HCID 69736995, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Trifluoroacetic acid 1 ml and water 0.1 ml were added to compound (34) 48.4 mg. The mixture was heated at 80° C. for 15 min and concentrated under reduced pressure. Ice-water was added to the residue, which was made alkaline with an aqueous saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was chromatographed on silica gel in ethyl acetate:hexane (1:2) to give the titled compound (35) as a colorless oil, 33.2 mg. Yield 78%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionIce-water was added to the residue, which
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas chromatographed on silica gel in ethyl acetate:hexane (1:2)

Sources & evidence

ORD record
ord-5b002fe2b46341b88a3c9b37213119a9
Source dataset
uspto-grants-2005_02
Patent number
US06858640B2

Reaction notes

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