Potassium Phosphate, Dibasic → 3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone

HRID 65439

Reaktionsgleichung

Reaktionsgleichung von HRID 65439
COC1C=CC(C[N:8]2[C@H:11]([S:12]([C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:14])=[O:13])[C@@H:10]([CH2:19][OH:20])[C:9]2=[O:21])=CC=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].P([O-])([O-])(O)=O.[K+].[K+]>C(#N)C.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[OH:20][CH2:19][C@@H:10]1[C@@H:11]([S:12]([C:15]([CH3:17])([CH3:16])[CH3:18])(=[O:14])=[O:13])[NH:8][C:9]1=[O:21]

Komponenten

8

Edukt 3

HCID 24450Potassium Phosphate, DibasicHCID 62655Sodium PersulfateHCID 186047721-p-methoxybenzyl-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone

Produkt 1

HCID 186047743-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 62662Ferrous sulfate heptahydrateKatalysatorHCID 165397Cupric acetate monohydrateKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 68.3 mg (0.2 mmol) of 1-p-methoxybenzyl-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone in 4 ml of acetonitrile is added to a solution of 428 mg (1.8 mmol) of sodium peroxydisulphate, 174 mg (1 mmol) of dipotassium hydrogen phosphate, 1 mg of iron(II) sulphate heptahydrate and 2 mg of copper(II) acetate hydrate in 4 ml of water. The mixture is stirred for 2 hours under an argon atmosphere at a bath temperature of 65°. The resulting mixture is then concentrated to half its volume under reduced pressure and extracted with ethyl acetate. The extract is triturated with methylene chloride and ether and the pure title compound is obtained.

Aufarbeitung

  1. concentrationThe resulting mixture is then concentrated to half its volume under reduced pressure
  2. extractionextracted with ethyl acetate
  3. customThe extract is triturated with methylene chloride and ether

Quellen und Nachweise

ORD-Eintrag
ord-139ed6457cd64e2e9fcb010d4805aeea
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04614614

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