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

HRID 433086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 433086
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-910f2490580e40c8b5bbc8d43b0fd89a
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06667301B2

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