7,10-Dioxa-2,5-diazaundecanoic acid, 4,9-dioxo-11-phenyl-, 9H-fluoren-9-ylmethyl ester Chemical Properties

Boiling point:

733.0±60.0 °C(Predicted)

Density 

1.269±0.06 g/cm3(Predicted)

pka

10.58±0.46(Predicted)

form 

Solid

color 

White to off-white

7,10-Dioxa-2,5-diazaundecanoic acid, 4,9-dioxo-11-phenyl-, 9H-fluoren-9-ylmethyl ester Usage And Synthesis

Uses

7,10-Dioxa-2,5-diazaundecanoic acid, 4,9-dioxo-11-phenyl-, 9H-fluoren-9-ylmethyl ester is an important organic intermediate. It can be used to synthesize camptothecin derivatives and other anticancer organic compounds, and then synthesize antibody-drug conjugate.

Definition

7,10-Dioxa-2,5-diazaundecanoic acid, 4,9-dioxo-11-phenyl-, 9H-fluoren-9-ylmethyl ester is also known as Benzyl 1-(9H-fluoren-9-yl)-3,6-dioxo-2,9-dioxa-4,7-diazaundecan-11-oate.

Preparation

(2-((((9H-fluorene-9-yl)methoxy)carbonyl)amino)acetamido)methyl acetate (7.36 g, 20.0 mmol), THF, and p-toluenesulfonic acid monohydrate (0.38 g, 2.00 mmol) were added to a single-neck bottle at 0°C. Benzyl glycolate (6.65 g, 40.0 mmol) was added dropwise and the temperature was naturally raised to room temperature for 2-4h. TLC monitoring this reaction. After the reaction was completed, saturated NaHCO3 solution was added to quench the reaction, extracted with ethyl acetate, and washed with saturated sodium chloride solution. After dried over anhydrous sodium sulfate, filtered, concentrated, and the residue was purified by column chromatography to obtain 7,10-Dioxa-2,5-diazaundecanoic acid, 4,9-dioxo-11-phenyl-, 9H-fluoren-9-ylmethyl ester.