Réaction #93073

Équation de réaction

tributylamine

N-hydroxybenzotriazole

dimethylaminopyridine

dimethylformamide

dimethylformamide

(aminothioxomethyl)hydrazine

dimethylformamide

→

dicyclohexylurea

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for 24 hours

Mode opératoire

[3S-[3α(Z),4α]]-3-[[(2-Amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid (0.66 g), 0.3 g of tributylamine, 0.26 g of N-hydroxybenzotriazole and 0.01 g of dimethylaminopyridine were dissolved in 10 ml of dimethylformamide and a solution of 0.33 g of N,N-dicyclohexylcarbodiimide in 5 ml of dimethylformamide was added. After stirring for 20 minutes at room temperature, a solution of 0.28 g of (aminothioxomethyl)hydrazine in 10 ml of dimethylformamide was also added. Stirring was continued for 24 hours, formed dicyclohexylurea was filtered off and the dimethylformamide of the filtrate was distilled off. The residue was dissolved in 20 ml tetrahydrofuran/methanol (1:1), filtered and a solution of 0.51 g of potassium perfluorobutanesulfonate in 5 ml of methanol was added followed by 20 ml of ether. The resultant precipitate of crude product was purified by column chromatography on HP-20 using water as an eluent and yielding 0.8 g of the title compound, melting point 218° C., (dec).

Source