m-Chloroperbenzoic acid → HCID 57119145, compound

HRID 2296362Notes

Reaction equation

HRID 2296362 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[C:17](=[CH:18][CH2:19][S:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:16][CH:15]2[N:12]1[C:13](=[O:28])[CH2:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:37])C=1>C(Cl)Cl>[CH2:1]([O:8][C:9]([CH:11]1[C:17](=[CH:18][CH2:19][S:20]([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:37])[O:16][CH:15]2[N:12]1[C:13](=[O:28])[CH2:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54182589HCID 54182589, compound

Product 1

HCID 57119145HCID 57119145, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl3-(2-benzylthioethylidene)-7-oxo-4-oxa-1-azabicyclo [3,2,0]heptane-2-carboxylate (39.5 mg) was dissolved in methylene chloride (5 ml) and treated with m-chloroperbenzoic acid (19 mg) at 0° C. The solution was stirred at 0° C. for 1/2 hour and washed with 3% bicarbonate solution (3×5 ml). The solvent was evaporated and the gum chromatographed to yield the title product as a mixture of R and S sulphoxides (30 mg; 73%).

Workup

  1. washwashed with 3% bicarbonate solution (3×5 ml)
  2. customThe solvent was evaporated
  3. customthe gum chromatographed

Sources & evidence

ORD record
ord-a46d119db1204dee8bcc14510395f218
Source dataset
uspto-grants-1984_01
Patent number
US04428958

Reaction notes

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