Trifluoroacetic acid → HCID 17858975, compound

HRID 1372662Notes

Reaction equation

HRID 1372662 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[CH:13][C:12]=1[CH3:25].FC(F)(F)C(O)=O>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][C:12]=1[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58778873HCID 58778873, compound

Product 1

HCID 17858975HCID 17858975, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (10 ml) was dissolved tert-butyl (4-(2-benzoxazolyl)amino-3-methylphenyl)acetate (1.17 g, 3.46 mmol). To the resulting solution was added trifluoroacetic acid (10 ml). The resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was poured in ice water, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform/methanol (60:1 to 50:1, v/v) eluate fractions, (4-(2-benzoxazolyl)amino-3-methylphenyl)acetic acid (924 mg, 95%) was obtained as a pale yellow solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform/methanol (60:1 to 50:1

Sources & evidence

ORD record
ord-4adf7d0049134f01848abe398d2ebd3b
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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