m-Chloroperbenzoic acid → diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate

HRID 232213Notes

Reaction equation

HRID 232213 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:15][O:14][N:13]([C:16]3([C:29]([O:31][CH:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])[CH:20](SC4C=CC=CC=4)[CH2:19][C:18](=[O:28])[O:17]3)[C:12]2=[O:45])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:15][O:14][N:13]([C:16]3([C:29]([O:31][CH:32]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:30])[CH:20]=[CH:19][C:18](=[O:28])[O:17]3)[C:12]2=[O:45])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67902355diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-3-phenylthio-2-tetrahydrofurancarboxylate

Product 1

HCID 67902310diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylateYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 3 ml of dichloromethane was dissolved 60 mg of the Compound (50) obtained in Example 50. To the solution was added 20 mg of 3-chloroperbenzoic acid. The mixture was stirred at room temperature for 30 minutes. The reaction solution was washed with an aqueous solution of sodium hydrogen carbonate and water, successively, followed by drying (Na2SO4). The solvent was then evaporated off, and the residue was dissolved in 1 ml of toluene. The solution was heated at 80° C. for 30 minutes, then the solvent was evaporated off. The residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 21 mg of the subject Compound (51) as colorless crystals. The IR and NMR spectra of this product were in agreement with those of the compound obtained in (a) above.

Workup

  1. washThe reaction solution was washed with an aqueous solution of sodium hydrogen carbonate and water
  2. dry with materialby drying (Na2SO4)
  3. customThe solvent was then evaporated off
  4. dissolutionthe residue was dissolved in 1 ml of toluene
  5. temperatureThe solution was heated at 80° C. for 30 minutes
  6. customthe solvent was evaporated off
  7. washfollowed by elution with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-410a2bb376a44cf1963afbf52657a90a
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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