(E)-(6R,7R)-7-(2-bromo-acetylamino)-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid → (E)-(6R,7R)-7-[2-[2-(3,4-Dihydroxy-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylsulfanyl]-acetylamino]-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Participants

Reaction Steps

(E)-(6R,7R)-7-(2-bromo-acetylamino)-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (see ex. C34a) (200.0 mg, 0.38 mmol) was dissolved in 4 ml N,N-dimethylformamide and 4-[7-mercapto-5-methyl-s-triazolo[1,5-a]pyrimidin-2-yl]pyrocatechol sodium salt (124.0 mg, 0.42 mmol) was added. After 5 h the reaction mixture was poured on diethyl ether and the suspension was filtered. The solid material was digerated with 10 ml ethyl acetate:water (1:1) for 1 h, filtered and dried in high vacuum.

Provenance & Evidence