Reaktion #93717

ord-139ed6457cd64e2e9fcb010d4805aeea

Reaktionsgleichung

COc1ccc(CN2C(=O)[C@H](CO)[C@H]2S(=O)(=O)C(C)(C)C)cc1
1-p-methoxybenzyl-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone
O=S(=O)([O-])OOS(=O)(=O)[O-].[Na+].[Na+]
sodium peroxydisulphate
O=P([O-])([O-])O.[K+].[K+]
dipotassium hydrogen phosphate
→
CC(C)(C)S(=O)(=O)[C@H]1NC(=O)[C@@H]1CO
title compound
CC(C)(C)S(=O)(=O)[C@H]1NC(=O)[C@@H]1CO
3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone

Edukte

COc1ccc(CN2C(=O)[C@H](CO)[C@H]2S(=O)(=O)C(C)(C)C)cc1
1-p-methoxybenzyl-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone
O=S(=O)([O-])OOS(=O)(=O)[O-].[Na+].[Na+]
sodium peroxydisulphate
O=P([O-])([O-])O.[K+].[K+]
dipotassium hydrogen phosphate

Reagenzien

O.O.O.O.O.O.O.O=S(=O)([O-])[O-].[Fe+2]
iron(II) sulphate heptahydrate
CC(=O)[O-].CC(=O)[O-].O.[Cu+2]
copper(II) acetate hydrate

Lösungsmittel

CC#N
acetonitrile
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04614614uspto-grants-1986_09