Reaktion #345614

Reaktionsgleichung

4-nitrobenzyl 2-[(3R,4R)-4-(p-toluenesulfonylthio)-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-methanesulfonyloxy-2-butenoate

triethylamine

→

title compound

Ausbeute 100.0%

4-Nitrobenzyl 2-[(3R,4R)-4-(p-toluenesulfonylthio)-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-2,3-butadienoate

Ausbeute 100.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeconsumption of the starting material
2. 2
   Waschenwith formation of a single new peak (eluting phase: 65% acetonitrile and 35% 0.01M phosphate pH 6.5 buffer)
3. 3
   workup.ADDITIONDilute hydrochloric acid (chilled at 0° C.) and ethyl acetate were added
4. 4
   WaschenThe organic layer was washed with cold water
5. 5
   Trocknendried (sodium sulfate)
6. 6
   Einengenconcentrated

Vorschrift

A solution of 4-nitrobenzyl 2-[(3R,4R)-4-(p-toluenesulfonylthio)-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-methanesulfonyloxy-2-butenoate (XVc, 0.0714 g, 0.00010 mole) in chloroform (1 mL) was treated with triethylamine (0.014 mL, 0.00010 mole) at room temperature. After a period of 1 h, reverse-phase C-18 HPLC indicated consumption of the starting material with formation of a single new peak (eluting phase: 65% acetonitrile and 35% 0.01M phosphate pH 6.5 buffer). Dilute hydrochloric acid (chilled at 0° C.) and ethyl acetate were added. The organic layer was washed with cold water, dried (sodium sulfate) and concentrated to give 0.0615 g (ca. 100%) of the title compound as a foam. The product was characterized by its 1H-NMR spectrum.

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