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Example 33. Bis(piperidineazepino)-6-((2-(2-(2-(2-(6-carboxyamido-2- cyanobenzothiazolyl)ethoxy)ethoxy)ethoxy)ethyl)carbamoyl)rhodamine (PBI 5122) [00194] To a solution of t-boc-N-amido-dPEG?4-acid (Quanta BioDesign, lg) and N- methylmorpholine (0.3 mL) in THF (25 mL), isobutyl chloroformate (0.36 mL) was added. After stirring for 30min, <strong>[7724-12-1]6-amino-2-cyanobenzothiazole</strong> (White et. al., J. Am. Chem. Soc. 88, 2015 (1966), 0.48g) was added, and the reaction stirred overnight. The reaction was then filtered, and the eluent concentrated. The crude reaction purified over silica gel (gradient of MeOH in CH2C12) to provide a clear oil (1.4 g).
Synthesis of linker-drugReferring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
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