Trifluoroacetic acid → HCID 21100737, compound

HRID 1352513Notes

Reaction equation

HRID 1352513 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:25]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:24][O:23][N:22]=2)=[CH:17][CH:16]=1)(C)(C)C>>[CH2:26]([C:25]1[C:21]([C:18]2[CH:17]=[CH:16][C:15]([NH2:14])=[CH:20][CH:19]=2)=[N:22][O:23][CH:24]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69422093HCID 69422093, compound

Product 1

HCID 21100737HCID 21100737, compoundYield 70%

Procedure

Trifluoroacetic acid (0.5 mL) is added to [4-(4-benzylisoxazol-3-yl)phenyl]carbamic acid tert-butyl ester (0.3 g) and stirred for 30 minutes. The reaction mixture is concentrated under reduced pressure and the concentrate is partitioned between ethyl acetate and 1N sodium hydroxide solution. The organic layer is washed with saturated sodium chloride, dried over anhydrous magnesium sulfate and chromatographed on silica gel (ethyl acetate/hexane as eluant) to give 0.15 g product as a white solid. MS: m/z 251 (M+H)+.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe concentrate is partitioned between ethyl acetate and 1N sodium hydroxide solution
  3. washThe organic layer is washed with saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customchromatographed on silica gel (ethyl acetate/hexane as eluant)

Sources & evidence

ORD record
ord-c517227dcce74e24ba87c98372128d96
Source dataset
uspto-grants-2007_05
Patent number
US07220768B2

Reaction notes

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