m-Chloroperbenzoic acid → HCID 86741704, compound

HRID 1788843Notes

Reaction equation

HRID 1788843 reaction equation
[CH2:1]([S:4][CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[S:11])[C:7](=[O:38])[CH2:6]1)[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:44]>C(OCC)(=O)C>[CH2:1]([S:4]([CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)[C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[S:11])[C:7](=[O:38])[CH2:6]1)=[O:44])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86741705HCID 86741705, compound

Product 1

HCID 86741704HCID 86741704, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4.0 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-fluorophenoxy)-3-trimethylacetylthio-propenate in ethyl acetate at -78° was added a solution of 1.5 g of 80% m-chloroperoxybenzoic acid in ethyl acetate over 10 minutes. The reaction mixture was washed with saturated sodium bicarbonate solution, dried over MgSO4, and evaporated in vacuo to dryness. Chromatography over silica gel and elution with ethyl acetate-hexane mixtures afforded 2.4 g of the title compound as a yellow oil (58% of the theoretical yield).

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo to dryness
  4. washChromatography over silica gel and elution with ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-682bf859e96f4071bbb1d613564a3977
Source dataset
uspto-grants-1987_08
Patent number
US04684640

Reaction notes

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