Reaktion #736881

Reaktionsgleichung

sodium benzenesulfinate

benzyl 2-[3-phenoxyacetamido-4-(6-nitrobenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoate

6-nitrobenzothiazol-2-yl benzenethiosulfonate

water

→

benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3-butenoate

Ausbeute 79.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe precipitated 6-nitrobenzothiazol-2-yl disulfide crystals were filtered
2. 2
   Einengenthe filtrate was concentrated under reduced pressure
3. 3
   workup.ADDITIONThe residue was treated in the same manner as in Example 1

Vorschrift

A 198 mg quantity of benzyl 2-[3-phenoxyacetamido-4-(6-nitrobenzothiazol-2-yldithio)-2-azetidinon-1-yl]-3-methyl-3-butenoate and 113 mg of 6-nitrobenzothiazol-2-yl benzenethiosulfonate were dissolved in 2.5 ml of acetone. To the solution were added 0.5 ml of water and then 3 mg of sodium benzenesulfinate. The mixture was stirred at room temperature for 8 hours. The precipitated 6-nitrobenzothiazol-2-yl disulfide crystals were filtered and the filtrate was concentrated under reduced pressure. The residue was treated in the same manner as in Example 1, giving benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3-butenoate in a yield of 79%. The NMR spectrum data of the compound thus obtained were identical with those of the compound produced in Example 3.

Quelle