Peracetic Acid → HCID 20162854, compound

HRID 246862Notes

Reaction equation

HRID 246862 reaction equation
[CH3:1][S:2][C:3]1([NH:8][C:9](=[O:18])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][NH:5][C:4]1=[O:7].C(OO)(=[O:21])C>O1CCOCC1.C(O)(=O)C>[CH3:1][S:2]([C:3]1([NH:8][C:9](=[O:18])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][NH:5][C:4]1=[O:7])=[O:21]

Participants

5

Reactant 2

HCID 6585Peracetic AcidHCID 20162876N-[3-(Methylsulfanyl)-2-oxoazetidin-3-yl]-2-phenoxyacetamide

Product 1

HCID 20162854HCID 20162854, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (25) (175 mg) in dry dioxan (7 ml) was treated with a solution of peracetic acid in glacial acetic acid (0.99 ml of a 5.07% w/v solution). The mixture was stirred at room temperature for approximately 20 mins, then evaporated to dryness. The residue was evaporated once more from dry dioxan before drying thoroughly in vacuo. The residue was taken up in chloroform and chromatographed on a short column of silica gel eluting with 10% meOH/CHCl3 to give the product (26) (186 mg) a mixture of sulphoxide isomers (approximately 1:2) νmax(CHCl3) 3410, 1785, 1690, and 1490 cm-1, δppm (CDCl3) (90 MHz) 2.60 (major isomer) and 2.67 (minor isomer) (both s, together 3H), 3.79 and 4.12 (ABq, minor isomer, J8 Hz) and 3.87 and 4.01 (ABq, major isomer, J6Hz) (together 2H), 4.53 (minor isomer) and 4.60 (major isomer) both s, together 2H), 6.52 (s, 1H, exch.), 6.80 to 7.45 (m, 5H), 7.78 (s, 1H, exch.).

Workup

  1. customevaporated to dryness
  2. customThe residue was evaporated once more from dry dioxan
  3. custombefore drying thoroughly in vacuo
  4. customchromatographed on a short column of silica gel eluting with 10% meOH/CHCl3

Sources & evidence

ORD record
ord-8bdf2af6ba0344179a5ef21659cfdfbf
Source dataset
uspto-grants-1987_11
Patent number
US04704385

Reaction notes

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