m-Chloroperbenzoic acid → HCID 131728041, compound

HRID 639768Notes

Reaction equation

HRID 639768 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:33])[CH2:22][CH2:23][C:24]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[O:25])[O:16][C:15]2=[O:34])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C1C=C(Cl)C=C(C(OO)=[O:43])C=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@@H:17]([CH2:19][NH+:20]([O-:43])[C:21](=[O:33])[CH2:22][CH2:23][C:24]([C:26]3[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=3)=[O:25])[O:16][C:15]2=[O:34])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 6482306HCID 6482306, compound

Product 1

HCID 131728041HCID 131728041, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (0-5° C.) of (S)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]-4-(4-chlorophenyl)-4-oxobutanamide, (1.150 gm, 0.0023 moles) in dichloromethane (150 ml) was added 60% m-CPBA (0.725 gm, 0.0040 moles) and the resulting solution stirred at room temperature for 12 hr. The solvent was evaporated under reduced pressure and the residue chromatographed over silica gel (100-200 mesh, 40 g). The column was eluted with ethyl acetate (200 ml) followed by a mixture of chloroform:methanol (4:1, 600 ml). Concentration of the combined fractions gave the title N-oxide (0.950 g, 80%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue chromatographed over silica gel (100-200 mesh, 40 g)
  3. washThe column was eluted with ethyl acetate (200 ml)
  4. additionfollowed by a mixture of chloroform:methanol (4:1, 600 ml)

Sources & evidence

ORD record
ord-23ddc3f578ef458d9b0540759afa07b9
Source dataset
uspto-grants-2010_04
Patent number
US07691889B2

Reaction notes

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