Zur Synthese von Maleoyl‐ und Glutaryl‐glycylchlorid

Abstract

Es wird iiber die Darstellung von Maleoyl-glycylchlorid (4), N-Chlorformylmethyl-maleinsaureamid-chlorid (5) und deren Anilide (6,7) sowie iiber Versuche zur Synthese von Glutarylglycylchlorid berichtet.N-Substituierte Maleinimide sind hinreichend bekannt, jedoch blieben bisher die Bemuhungen, den Maleoylrest als Schutzgruppe fur Aminosauren einzufuhren, erfolglos*.z). Fur (3-Lactamsynthesen benotigten wir Maleoyl-glycylchlorid. Dazu haben wir, ahnlich wie King und Mitarbb.l), aus Maleinsaureanhydrid (1) und Glycin 176*

Synthesis of photoactivatable fluorescein derivatives bearing side chains with varying properties

“…Displacement with sodium iodide in acetone then gave the iodoacetyl hydrazone 25. With these results in hand, completion of the synthesis of the target compounds 4 and 5 was straightforward oia hydrazone formation between the aldehyde 13 and the respective hydrazides. Thus, compound 4 was obtained directly, while for compound 5 initial condensation of the aldehyde 13 and the chloroacetyl hydrazide 23 was followed by displacement with NaI-acetone.…”

“…over 1 h. It was then kept for a further 1 h and then diluted with CH,Cl,, washed with water and brine, dried (Na,SO,) and evaporated under reduced pressure. The residue was purified by flash chromatography [EtOAc-light petroleum (1 : l)] to afford the aldehyde 13 The aldehyde 13 (82 mg) was dissolved in DMF (0.4 cm3) and treated with a solution of the maleimide 19 (75 mg, 0.21 5 mmol) in EtOH (0.65 cm3) and 2 mol dm-, aq. NaOAc (0.125 cm3).…”