تفاعل #93715

ord-aa853de2f5c04505a7cd89b5973f20c2

معادلة التفاعل

COc1ccc(CN2C(=O)[C@H](CO)[C@H]2S(=O)(=O)C(C)(C)C)c(OC)c1
1-(2,4-dimethoxybenzyl)-3-(S)-hydroxymethyl-4-(R)-tert.butylsulphonyl-2-azetidinone
O=S(=O)([O-])OOS(=O)(=O)[O-].[K+].[K+]
potassium 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

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىthe resulting reaction mixture
  2. 2
    استخلاصthe aqueous residue is extracted with ethyl acetate
  3. 3
    تجفيفAfter drying of the organic phase over Na2SO4 and concentration by evaporation in vacuo

الإجراء التجريبي

A solution of 74 mg (0.2 mmol) of 1-(2,4-dimethoxybenzyl)-3-(S)-hydroxymethyl-4-(R)-tert.butylsulphonyl-2-azetidinone (see Example 20), 486 mg (1.8 mmol) of potassium peroxydisulphate and 174 mg (1.0 mmol) of dipotassium hydrogen phosphate in 4 ml of acetonitrile is stirred for 2 hours at 65° under a reflux condenser, the resulting reaction mixture is freed from acetonitrile under reduced pressure and the aqueous residue is extracted with ethyl acetate. After drying of the organic phase over Na2SO4 and concentration by evaporation in vacuo, a residue is obtained from which the title compound is obtained in the form of colourless crystals by adding a little methylene chloride and ether.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04614614uspto-grants-1986_09