Trifluoroacetic acid → HCID 54340399, compound

HRID 35582Notes

Reaction equation

HRID 35582 reaction equation
C([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([CH:15]=[C:16]([CH2:22][CH3:23])[CH:17]([N+:19]([O-:21])=[O:20])[CH3:18])[C:12]([NH2:14])=[O:13])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>>[C:6]([CH2:8][O:9][N:10]=[C:11]([CH:15]=[C:16]([CH2:22][CH3:23])[CH:17]([N+:19]([O-:21])=[O:20])[CH3:18])[C:12]([NH2:14])=[O:13])([OH:7])=[O:5]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 537673582-t-Butoxycarbonylmethoxyimino-4-ethyl-5-nitro-3-hexenamide

Product 1

HCID 54340399HCID 54340399, compoundYield 48.2%

Procedure

2-t-Butoxycarbonylmethoxyimino-4-ethyl-5-nitro-3-hexenamide (80 mg) was treated with trifluoroacetic acid (1 ml) at ambient temperature for 2 hours. Excess trifluoroacetic acid was distilled off under reduced pressure to give a residue which was purified by preparative thin layer chromatography, eluting with a mixture of benzene, dioxane and acetic acid (14:5:1) to give 2-carboxymethoxyimino-4-ethyl-5-nitro-3-hexenamide (32 mg).

Workup

  1. distillationExcess trifluoroacetic acid was distilled off under reduced pressure
  2. customto give a residue which
  3. customwas purified by preparative thin layer chromatography
  4. washeluting with a mixture of benzene, dioxane and acetic acid (14:5:1)

Sources & evidence

ORD record
ord-436fe5bb3bf5417d81a8089400eb96de
Source dataset
uspto-grants-1988_08
Patent number
US04767768

Reaction notes

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