FK 3311 → 4'-[1-(Tert-butyloxycarbonylmethoxyimino)ethyl]-2'-(2,4-difluorophenoxy)methanesulfonanilide

HRID 1607685Notes

Reaction equation

HRID 1607685 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:6]([O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:5]=1)(=O)[CH3:2].[NH2:24][O:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>C(O)C>[C:30]([O:29][C:27]([CH2:26][O:25][N:24]=[C:1]([C:4]1[CH:14]=[CH:13][C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:6]([O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:5]=1)[CH3:2])=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 164009FK 3311HCID 12919121tert-Butyl (aminooxy)acetate

Product 1

HCID 543214524'-[1-(Tert-butyloxycarbonylmethoxyimino)ethyl]-2'-(2,4-difluorophenoxy)methanesulfonanilideYield 125.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4'-acetyl-2'-(2,4-difluorophenoxy)methanesulfonanilide (1.5 g) and tert-butyl aminooxyacetate (0.71 g) in ethanol (5 ml) was refluxed for 13 hours. The mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residual oil was suspended in ether and the insoluble material was filtered off. The filtrate was concentrated to give an cil of 4'-[1-(tertbutyloxycarbonylmethoxyimino)ethyl]-2'-(2,4-difluorophenoxy)methanesulfonanilide (2.6 g).

Workup

  1. temperaturewas refluxed for 13 hours
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe insoluble material was filtered off
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4bf3df6cc27f4952a4b45185a42c5c9a
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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