m-Chloroperbenzoic acid → HCID 67502424, compound

HRID 1187781Notes

Reaction equation

HRID 1187781 reaction equation
[CH3:1][C:2]1([CH3:31])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]3[N:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][N:24]=3)=[CH:18][CH:17]=2)[CH2:4][O:3]1.C1C=C(Cl)C=C(C(OO)=[O:40])C=1>ClCCl.[O-]S([O-])=O.[Na+].[Na+]>[CH3:1][C:2]1([CH3:31])[N:6]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@@H:5]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]3[N:24]=[CH:25][C:26]([S:29]([CH3:30])=[O:40])=[CH:27][N:28]=3)=[CH:18][CH:17]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67514192HCID 67514192, compound

Product 1

HCID 67502424HCID 67502424, compoundYield 111.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24437Sodium SulfiteSolvent

Procedure

To a stirred solution of (5)-tert-butyl 2,2-dimethyl-4-(4-(5-(methylthio)pyrimidin-2-ylamino)phenethyl)oxazolidine-3-carboxylate (393 mg) in dichloromethane (5 ml) was added m-CPBA (218 mg) and stirring was continued at RT for 40 min. The reaction mixture was then diluted with aq. Na2SO3 solution and extracted with dichloromethane. The organic layers were dried over MgSO4 and concentrated in vacuo to give (4S)-tert-butyl 2,2-dimethyl-4-(4-(5-(methylsulfinyl)pyrimidin-2-ylamino)phenethyl)oxazolidine-3-carboxylate (454 mg, 85% purity, 95% yield) as a yellow oil. MS (ISP): 461.4 ([M+H]+), 405.3 ([M+H—C4H8—CO2]+).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b52a0ea522c43fe92c03974cfb9bb8e
Source dataset
uspto-grants-2014_03
Patent number
US08673950B2

Reaction notes

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