Pentafluorophenyl Trifluoroacetate → Pentafluorophenyl pyridine-2-carboxylate

Beteiligte Stoffe

Reaktionsschritte

Using analogous procedures to those described in Example 12, 5-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]pyridine-2-carboxylic acid was reacted with pentafluorophenyl trifluoroacetate to give the pentafluorophenyl pyridine-2-carboxylate which was in turn reacted with tri-tert-butyl L-γ-glutamyl-D-glutamate (European Patent Application No. 0509643, Example 1 thereof) to give tri-tert-butyl N-{5-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]pyridyl-2-carbonyl -L-γ-glutamyl-D-glutamate in 98% yield which was in turn hydrolysed with aqueous sodium hydroxide solution to give N-{5-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]pyridyl-2-carbonyl}-L-γ-glutamyl-D-glutamic acid in 68% yield, m.p. 196° C.;

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