Formic Acid → 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetic acid

HRID 1022840Notes

Reaction equation

HRID 1022840 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][O:8]/[N:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:21][C:20]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=3)([C:22]([F:25])([F:24])[F:23])[O:19][N:18]=2)=[CH:13][C:12]=1[CH3:34])(C)(C)C.C(O)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:33][C:28]1[CH:27]=[C:26]([C:20]2([C:22]([F:24])([F:23])[F:25])[O:19][N:18]=[C:17]([C:14]3[CH:15]=[CH:16][C:11](/[CH:10]=[N:9]/[O:8][CH2:7][C:6]([OH:35])=[O:5])=[C:12]([CH3:34])[CH:13]=3)[CH2:21]2)[CH:31]=[C:30]([Cl:32])[CH:29]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 6422Trifluoroacetic acidHCID 87403035tert-butyl 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetate2×

Product 1

HCID 467018012-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetic acidYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [1-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-meth-(E)-ylideneaminooxy]-acetic acid tert-butyl ester (i.e the product of Step 1, 531 mg) in CH2Cl2 (20 mL) was treated with formic acid (0.25 mL, 0.30 g) and stirred at room temperature over night. Trifluoroacetic acid (0.50 g) was added and the mixture stirred until tlc (thin layer chromatography) indicated completion of the reaction. The organic layer was washed with water three times, dried (Na2SO4) and evaporated to give the title compound (502 mg, 80%) that was used in the next step without further purification. NMR indicated the absence of the tert butyl ester.

Workup

  1. stirringthe mixture stirred until tlc (thin layer chromatography)
  2. customcompletion of the reaction
  3. washThe organic layer was washed with water three times
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-25f165343bd8469c91d255123743b6ea
Source dataset
uspto-grants-2014_05
Patent number
US08722673B2

Reaction notes

Loading…