m-Chloroperbenzoic acid → HCID 131728039, compound

HRID 639767Notes

Reaction equation

HRID 639767 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:36])[CH2:22][CH2:23][C:24]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)=[O:25])[O:16][C:15]2=[O:37])[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:46])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-:46])[C:21](=[O:36])[CH2:22][CH2:23][C:24]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)=[O:25])[O:16][C:15]2=[O:37])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 6482308HCID 6482308, compound

Product 1

HCID 131728039HCID 131728039, compoundYield 89.9%

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-(2-naphthyl)-4-oxobutanamide (0.950 gm, 0.0019 moles) in dichloromethane (150 ml) was added 60% m-CPBA (0.550 g, 0.0032 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 the combined fractions gave the title N-oxide (0.891 g, 82%) 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)
  5. concentrationConcentration the combined fractions

Sources & evidence

ORD record
ord-f8c45f2a6ba34c6888626f6a78a6ed1c
Source dataset
uspto-grants-2010_04
Patent number
US07691889B2

Reaction notes

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