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

HRID 2089129Notes

Reaction equation

HRID 2089129 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[CH:5][C:6]2[O:10][N:9]=[C:8]([NH2:11])[C:7]=2[CH:12]=1.O.[C:16]([OH:20])(=[O:19])[CH:17]=O.CC(O)=O>CO>[F:14][C:2]([F:1])([F:13])[C:3]1[CH:4]=[CH:5][C:6]2[O:10][N:9]=[C:8]([NH:11][CH2:17][C:16]([OH:20])=[O:19])[C:7]=2[CH:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 15620607Glyoxylic acid, monohydrateHCID 438110995-(Trifluoromethyl)-1,2-benzoxazol-3-amine

Product 1

HCID 58548759(5-Trifluoromethyl-benzo[d]isoxazol-3-ylamino)-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

5-Trifluoromethyl-benzo[d]isoxazol-3-ylamine (2.5 g, 12.4 mmol) and glyoxylic acid monohydrate (Aldrich, 1.14 g, 12.4 mmol) in MeOH (10 mL) were treated with a few drop of AcOH and heated at 80° C. for 30 min. The reaction was then cooled to room temperature and NaBCNH3 (Aldrich, 1.17 g, 18.6 mmol) was added in one portion and the resulting solution was stirred at room temperature for another 2 hours. The solvent was removed and the residue was partitioned between ether and 1 N NaOH. The aqueous layer was then acidified with 1 N HCl to pH=3 and then extracted three times with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title compound as white solid.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. additionNaBCNH3 (Aldrich, 1.17 g, 18.6 mmol) was added in one portion
  3. customThe solvent was removed
  4. customthe residue was partitioned between ether and 1 N NaOH
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7899549d784d48daa438b804fc2466ec
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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