Reaktion #54311

Reaktionsgleichung

3-acetyloxy-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

4-benzyloxycarbonyl-2-vinylglutamic acid chloride

ethyl acetate

→

7-[[2-amino-4-carboxy-2-vinylbutyryl]amino]-3-acetyloxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis refluxed for 2 hours after which the solvent
2. 2
   Sonstigeis removed
3. 3
   Sonstigeleaving a residue which
4. 4
   workup.ADDITIONis treated with mild acid
5. 5
   Sonstigechromatographed on silica gel

Vorschrift

A mixture of 1 gram of 3-acetyloxy-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and 1 g of 4-benzyloxycarbonyl-2-vinylglutamic acid chloride wherein the free amino group is protected with tert-butoxycarbonyl in 50 ml of ethyl acetate is refluxed for 2 hours after which the solvent is removed leaving a residue which is treated with mild acid and chromatographed on silica gel using benzene-acetone as the eluant to give 7-[[2-amino-4-carboxy-2-vinylbutyryl]amino]-3-acetyloxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Quelle