m-Chloroperbenzoic acid → 5-(S)-azidomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

HRID 2305672Notes

Reaction equation

HRID 2305672 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[N:12]([CH2:15][C@H:16]1[O:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[C:24]([F:30])[CH:23]=2)[CH2:17]1)=[N+:13]=[N-:14]>C(Cl)Cl>[N:12]([CH2:15][C@H:16]1[O:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:29])=[O:6])=[C:24]([F:30])[CH:23]=2)[CH2:17]1)=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 229662145-(S)-Azidomethyl-3-[4'-methylthio-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 229662135-(S)-azidomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperoxybenzoic acid (77%, 0.079 g, 0.354 mmol) was added portionwise with stirring to a solution of 5-(S)-azidomethyl-3-[4′-methylthio-3′-fluorophenyl]oxazolidine-2-one (0.100 g, 0.354 mmol) in DCM (4 ml) at 0° C. The mixture was allowed to warm up to r.t. over 2 h. The mixture was washed with aq. saturated sodium bicarbonate, brine, dried (MgSO4), and evaporated to give product as a white solid (0.100 g, 95%). MS (m/z): [M+H]+=299.

Workup

  1. washThe mixture was washed with aq. saturated sodium bicarbonate, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-8025fd4207c14e2896dfb23c1a7e303e
Source dataset
uspto-grants-2002_08
Patent number
US06441005B1

Reaction notes

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