Reaktion #10292

Reaktionsgleichung

sodium carbonate

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

potassium peroxymonosulfate

→

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

Lösungsmittel

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with diethyl ether (20 mL)
2. 2
   TrocknenThe organic phase was dried (magnesium sulfate)
3. 3
   Einengenconcentrated
4. 4
   SonstigePurification of the residue by silica gel chromatography with 10% ethyl acetate in chloroform

Vorschrift

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.

Quelle