Trifluoroacetic acid → (5-Trifluoromethyl-benzo[d]isoxazol-3-ylamino)-acetic acid

HRID 2225211Notes

Reaction equation

HRID 2225211 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[CH:5][C:6]2[O:10][N:9]=[C:8]([NH:11][CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[C:7]=2[CH:20]=1.FC(F)(F)C(O)=O>ClCCl>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:4]=[CH:5][C:6]2[O:10][N:9]=[C:8]([NH:11][CH2:12][C:13]([OH:15])=[O:14])[C:7]=2[CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69286599Tert-butyl 2-(5-(trifluoromethyl)benzo[d]isoxazol-3-ylamino)acetate

Product 1

HCID 58548759(5-Trifluoromethyl-benzo[d]isoxazol-3-ylamino)-acetic acidYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation I7, Step 5: A solution of tert-butyl 2-(5-(trifluoromethyl)benzo[d]isoxazol-3-ylamino)acetate (367 mg) in dichloromethane (20 mL) at 0° C. was treated with trifluoroacetic acid (2 mL) and stirred at rt for 5 h. The mixture was concentrated under vacuum, and the residue was purified by column chromatography on silica gel, eluting with 10% to 50% (v/v) ethyl acetate-hexane, to provide 2-(5-(trifluoromethyl)benzo[d]isoxazol-3-ylamino)acetic acid (270 mg) as an off-white solid. MS found: (M+H)+=261.

Workup

  1. customPreparation I7, Step 5
  2. concentrationThe mixture was concentrated under vacuum
  3. customthe residue was purified by column chromatography on silica gel
  4. washeluting with 10% to 50% (v/v) ethyl acetate-hexane

Sources & evidence

ORD record
ord-b1981d1126494c00b7423d75da26b8df
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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