m-Chloroperbenzoic acid → HCID 67502792, compound

HRID 1187782Notes

Reaction equation

HRID 1187782 reaction equation
[CH3:1][C:2]1([CH3:32])[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]([CH3:31])=[O:30])=[CH:25][N:24]=3)=[CH:18][CH:17]=2)[CH2:4][O:3]1.C1C=C(Cl)C=C(C(OO)=[O:41])C=1>ClCCl.[O-]S([O-])=O.[Na+].[Na+]>[CH3:1][C:2]1([CH3:32])[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:28]=[CH:27][C:26]([S:29]([CH3:31])(=[O:41])=[O:30])=[CH:25][N:24]=3)=[CH:18][CH:17]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67502424HCID 67502424, compound

Product 1

HCID 67502792HCID 67502792, compoundYield 114.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24437Sodium SulfiteSolvent

Procedure

To a stirred solution of (4S)-tert-butyl 2,2-dimethyl-4-(4-(5-(methylsulfinyl)pyrimidin-2-ylamino)phenethyl)oxazolidine-3-carboxylate (227 mg) in dichloromethane (5 ml) was added m-CPBA (155 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 (S)-tert-butyl 2,2-dimethyl-4-(4-(5-(methylsulfonyl)pyrimidin-2-ylamino)phenethyl)oxazolidine-3-carboxylate (269 mg, 70% purity, 94% yield) as a brown oil. MS (ISP): 477.4 ([M+H]+), 421.3 ([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-c9aec9c33efc48e5bacbb46b413b46dd
Source dataset
uspto-grants-2014_03
Patent number
US08673950B2

Reaction notes

Loading…