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

HRID 10196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 10196
[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-305d8ec7c91040e88056b133c1815a61
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094778B2

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