m-Chloroperbenzoic acid → HCID 86741702, compound

HRID 1788840Notes

Reaction equation

HRID 1788840 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]([O:37][CH3:38])=[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:39])[CH2:6]1)[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:45]>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]([O:37][CH3:38])=[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:39])[CH2:6]1)=[O:45])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86741703HCID 86741703, compound

Product 1

HCID 86741702HCID 86741702, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 0.35 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-methoxyphenoxy)-3-trimethylacetylthio-propenate in ethyl acetate at -78° C. was added a solution of 0.128 g of 80% m-chloroperoxybenzoic acid in ethyl acetate over 10 minutes. The reaction mixture was washed with saturated sodium bicarbonate solution, was dried over MgSO4 and evaporated in vacuo to dryness. Chromatography over silica gel and elution with ethyl acetate-hexane mixtures afforded 0.223 g of the title compound as a yellow oil (62% of the theoretical yield).

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  2. dry with materialwas dried 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-0bc59737e03a4de3845a019af7b8aba5
Source dataset
uspto-grants-1987_08
Patent number
US04684640

Reaction notes

Loading…