Dimethylaminoethyl esters hydrolysis

Dimethylaminoethane-2-ol (20) is a compound that, by virtue of its nucleophilic center (Me2NH+C2H40), is employed to convert protected segments bound to supports as benzyl esters into acids by transesterification into dimethylaminoethyl esters [C(=0)0C2H4NMe2] that are hydrolyzable by a dimethylformamide-water (1 1) mixture. Compound 20 readily forms esters from acid chlorides. The hydrolysis and esterification are facilitated by anchimeric assistance by the adjacent nitrogen atom (see Section 2.10). The amino alcohol also reacts with dichloromethane. 

Instead of the not necessarily harmless saponification with alkali, in 1973 M.A. Barton and her associates proposed an elegant procedure cleavage of the peptide from the supporting polymer by intramolecularly catalyzed transesterification of the (benzyl) ester bond with dimethylaminoethanol followed by the anchimerically assisted hydrolysis of the peptide dimethylaminoethyl ester. 

The attack by the nucleophile, dimethylaminoethanol, is followed by hydrolysis of the dimethylaminoethyl ester with water under relatively mild conditions general base catalysis is provided by the tertiary amino group in the ester portion of the molecule ... 

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