Triethylamine → Phenyl 1-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo(3,2,0)hept-2-en-6-yl)-1-(p-nitrobenzyloxycarbonyl)-prop-1-en-2-yl phenylphosphonate

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Reaction Conditions

Reaction Steps

To a stirred solution of p-nitrobenzyl α-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo(3,2,0)hept-2-en-6-yl)-α-(1-hydroxyethylidene)acetate (4.69 g) in tetrahydrofuran (60 ml.) under a nitrogen atmosphere at 0° C. was added triethylamine (1.6 ml.) followed by phenyl phenylphosphonochloridate (2.91 g). After stirring for 3 hours at 20° C., the tetrahydrofuran was evaporated and the residue dissolved in dichloromethane. The resulting solution was washed with 1% hydrochloric acid and then water, dried with magnesium sulphate and evapoated to give the title compound as a pale yellow friable foam in essentially quantitative yield. TLC (silica)Rf 0.64 (ethyl acetate). NMR δCDCl3 2.60 (m, 3H), 3.70-4.67 (m, 2H), 5.15 (s, 2H), 5.57-5.87 (m, 2H) and 6.6-8.17 (m, 19H).

Provenance & Evidence