Trifluoroacetic acid → 4'-[1-(Carboxymethoxyimino)ethyl]-2'-(2,4-difluorophenoxy)methanesulfonanilide

HRID 1607686Notes

Reaction equation

HRID 1607686 reaction equation
C([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:13]1[CH:23]=[CH:22][C:16]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[C:15]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])[CH:14]=1)[CH3:12])=[O:7])(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[C:6]([CH2:8][O:9][N:10]=[C:11]([C:13]1[CH:23]=[CH:22][C:16]([NH:17][S:18]([CH3:21])(=[O:19])=[O:20])=[C:15]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])[CH:14]=1)[CH3:12])([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 543214524'-[1-(Tert-butyloxycarbonylmethoxyimino)ethyl]-2'-(2,4-difluorophenoxy)methanesulfonanilide

Product 1

HCID 539552194'-[1-(Carboxymethoxyimino)ethyl]-2'-(2,4-difluorophenoxy)methanesulfonanilideYield 65.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4'-[1-(tert-butyloxycarbonylmethoxyimino)ethyl]-2'-(2,4-difluorophenoxy)methanesulfonanilide (2.6 g), anisole (2 ml), and trifluoroacetic acid (6 ml) in dichloromethane (50 ml) was stirred for 5 hours at room temperature. The mixture was concentrated, and the residue was dissolved in an aqueous solution of sodium bicarbonate and washed with ethyl acetate. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated under reduced pressure. The residue was recrystallized from a mixture of hexane and ethyl acetate to give pale yellow powder of 4'-[1-(carboxymethoxyimino)ethyl]-2'-(2,4-difluorophenoxy)methanesulfonanilide (1.5 g).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in an aqueous solution of sodium bicarbonate
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-49dae993cc4444318c438ae8d13167d5
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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