Sodium Carbonate → 3-(4-{ethyl-[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]amino}butyl)-[1,3]oxazinan-2-one

HRID 900663Notes

Reaction equation

HRID 900663 reaction equation
[CH2:1]([N:3]([C@@H:15]([CH3:25])[CH2:16][C:17]1[CH:22]=[CH:21][C:20](SC)=[CH:19][CH:18]=1)[CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH2:11][O:10][C:9]1=[O:14])[CH3:2].[S:26]([O-:31])(O[O-])(=O)=[O:27].[K+].[K+].[C:34](=O)([O-])[O-].[Na+].[Na+]>CO.O>[CH2:1]([N:3]([C@@H:15]([CH3:25])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([S:26]([CH3:34])(=[O:31])=[O:27])=[CH:21][CH:22]=1)[CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH2:11][O:10][C:9]1=[O:14])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10313463Potassium peroxymonosulphateHCID 692253143-(4-{ethyl-[(S)-2-(4-methylsulfanyl-phenyl)-1-methylethyl]amino}butyl)-[1,3]oxazinan-2-one

Product 1

HCID 692232353-(4-{ethyl-[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]amino}butyl)-[1,3]oxazinan-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To an ice cooled solution of 3-(4-{ethyl-[(S)-2-(4-methylsulfanylphenyl)-1-methylethyl]amino}butyl)-[1,3]oxazinan-2-one (0.33 g, 0.9 mmole) in methanol (10 mL) was added a solution of potassium peroxymonosulfate (Oxone®) (1.22 g, 1.98 mmole) in water (10 mL). The reaction mixture was stirred at room temperature for 5 hours. Then 1.5M sodium carbonate solution (10 mL) was added and the mixture was extracted with diethyl ether (20 mL). The organic phase was dried (magnesium sulfate) and concentrated. Purification of the residue by silica gel chromatography with 10% ethyl acetate in chloroform, gave 3-(4-{ethyl-[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]amino}butyl)-[1,3]oxazinan-2-one, 122, (0.17 g) as a colorless oil. Anal.: Calcd. for C20H33ClN2O4S: C, 55.48; H, 7.68; N, 6.47%. Found C, 52.32; H, 7.42; N, 5.97.

Workup

  1. extractionthe mixture was extracted with diethyl ether (20 mL)
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. concentrationconcentrated
  4. customPurification of the residue by silica gel chromatography with 10% ethyl acetate in chloroform

Sources & evidence

ORD record
ord-a31d8c201f6d43ca83feed8399f097f3
Source dataset
uspto-grants-2008_04
Patent number
US07361648B2

Reaction notes

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