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ChemicalBook CAS DataBase List Mal-Amido-PEG4-acid
1263045-16-4

Mal-Amido-PEG4-acid synthesis

4synthesis methods
-

Yield:1263045-16-4 0.227 g

Reaction Conditions:

Stage #1: 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acidwith 4-nitrophenylglyoxylic acid in dichloromethane at 20;
Stage #2: 3-maleimidopropionic acid N-hydroxysuccinimide esterwith N-ethyl-N,N-diisopropylamine in dichloromethane at 20;

Steps:

1 Synthesis of linker-drug

Synthesis of linker-drug
Referring 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.

References:

WO2015/196089,2015,A1 Location in patent:Paragraph 0273; 0281

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