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

HRID 351896Notes

Reaction equation

HRID 351896 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([NH:15][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:31])=[O:30])=[C:25]([F:32])[CH:24]=2)[CH2:18]1)(=[O:14])[CH3:13]>C(Cl)Cl>[C:12]([NH:15][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:31])(=[O:6])=[O:30])=[C:25]([F:32])[CH:24]=2)[CH2:18]1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 229661925-(S)-Acetamidomethyl-3-[4'-methylsulfinyl-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 229661935-(S)-Acetamidomethyl-3-[4'-methylsulfonyl-3'-fluorophenyl]oxazolidine-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperoxybenzoic acid (77%, 0.0784 g, 0.350 mmol) was added portionwise to a solution of 5-(S)-Acetamidomethyl-3-[4′-methylsulfinyl-3′-fluorophenyl]oxazolidine-2-one (0.110 g, 0.350 mmol) in DCM (20 ml) at r.t. The mixture was stirred for 2 h, then washed with aq. saturated sodium bicarbonate, brine, dried (MgSO4), and evaporated to give product as a white solid (0.106 g, 92%). MS (m/z): [M+H]+=331.

Workup

  1. washwashed with aq. saturated sodium bicarbonate, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-32b223c2dc6e4f73860e5888f02ce019
Source dataset
uspto-grants-2004_06
Patent number
US06743811B2

Reaction notes

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