m-Chloroperbenzoic acid → HCID 88666459, compound

HRID 330708Notes

Reaction equation

HRID 330708 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:32]/[O:33][CH3:34])/[C:12]([NH:14][C:15]2(SC)[CH2:19][O:18][N:17]([C:20]3([C:26]([O-:28])=[O:27])[CH2:24][CH2:23][C:22](=[O:25])[O:21]3)[C:16]2=[O:29])=[O:13])[N:10]=1)=[O:4].Cl[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([C:42](OO)=O)[CH:37]=1>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:32]/[O:33][CH3:34])/[C:12]([NH:14][CH:15]2[CH2:19][O:18][N:17]([C:20]3([C:26]([O:28][CH:42]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:38]4[CH:39]=[CH:40][CH:41]=[CH:36][CH:37]=4)=[O:27])[CH2:24][CH2:23][C:22](=[O:25])[O:21]3)[C:16]2=[O:29])=[O:13])[N:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178502807HCID 178502807, compound

Product 1

HCID 88666459HCID 88666459, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 4 ml of dry methylene chloride was dissolved 210 mg of 2-{(4RS)-4-[2-(2-chloroacetamido-4-thiazolyl)-(Z)-2(methoxyimino)acetamido]-4-methylthio-3-oxo-2-isoxazolidinyl}-5-oxo-2-tetrahydrofuran carboxylate. To the solution was added 145 mg of m-chloroperbenzoic acid, and the reaction was allowed to proceed at room temperature for 20 hours. The reaction solution was concentrated under reduced pressure, and the concentrate was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate was subjected to a silica-gel column chromatography, eluting with ethyl acetate - n-hexane (1:1) to give 162 mg of the above-titled Compound (30a).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe concentrate was dissolved in ethyl acetate
  3. washThe solution was washed with an aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with ethyl acetate - n-hexane (1:1)

Sources & evidence

ORD record
ord-36ae70154482416e8c201e2d36b5f389
Source dataset
uspto-grants-1990_01
Patent number
US04897489

Reaction notes

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