m-Chloroperbenzoic acid → HCID 70478871, compound

HRID 2296363Notes

Reaction equation

HRID 2296363 reaction equation
[CH2:1]([S:3][CH2:4][CH:5]=[C:6]1[O:12][CH:11]2[N:8]([C:9](=[O:13])[CH2:10]2)[CH:7]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH3:2].ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)Cl>[CH2:1]([S:3]([CH2:4][CH:5]=[C:6]1[O:12][CH:11]2[N:8]([C:9](=[O:13])[CH2:10]2)[CH:7]1[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])=[O:32])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70478697HCID 70478697, compound

Product 1

HCID 70478871HCID 70478871, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl 3-(2-ethylthioethylidene)-7-oxo-4-oxa-1-azabicyclo[3,2,0]heptane-2-carboxylate (704 mg) was dissolved in methylene chloride (40 ml) and treated with m-chloroperbenzoic acid (370 mg). The solution was stirred at 0° C. for 1.0 hour and washed with a dilute bicarbonate solution (×2). The extract was dried over MgSO4 and evaporated. Chromatography over silica gel yielded the title product as a mixture of R and S sulphoxides (295 mg);

Workup

  1. washwashed with a dilute bicarbonate solution (×2)
  2. dry with materialThe extract was dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-7aa404bd8c104d10a1f0bff20650335c
Source dataset
uspto-grants-1984_01
Patent number
US04428958

Reaction notes

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