Dimethylaminoethyl ester

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. 

Eisleb, O. (Winthrop) Beta-Dimethylaminoethyl ester of para-butylamino-benzoic acid, US 1889645 (1932). 

Estimate the Ki0Vi values at 25°C of the following compounds based on the experimental Ki0Vi values of the indicated structurally related compounds (a) benzoic acid dimethylaminoethyl ester from benzoic acid ethyl ester (log Kiaw = 2.64), (b) the insecticide methoxychlor from DDT (log Ki0Vi = 6.20), (c) the insecticide fenthion from parathion [log Kiow = 3.83, see 111. Ex. 7.2, Answer (d)], and (d) the hormone estradiol from testosterone [log Ki0Vi = 3.32, see 111. Ex. 7.2, Answer (e)]. 

D.W. Johnson, Dimethylaminoethyl esters for trace, rapid analysis of fatty acids by ESI-MS-MS, Rapid Cormnun. Mass Spectrom., 13 (1999) 2388. 

Prepared by the polymerization of acrylic and methacrylic acids or their esters, e.g. butyl ester or dimethylaminoethyl ester. 

Several carboxylic acid derivatives of ll-deoxy-13,14-dihy-dro-PGEi (237) were prepared via the acid chloride 258 and are listed in Table V. In addition the decyl ester 264 and the dimethylaminoethyl ester 265 of 15-deoxy-16-hydroxy-PGE2 were obtained by the mixed anhydride method (111.112). 

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 ... 

Figure 4 ESI-MS/MS analysis of the acetyl dimethylaminoethyl esters extracted from 3mm dried blood spots. A neutral loss of 60 Da scan is shown for (A) a control blood spot, and (B) a blood spot from a patient with peroxisome biogenesis defect (Zellweger syndrome variant). The x-axis shows the molecular weights of the protonated molecular ions that lose acetic acid. Reproduced with permission from Johnson DW, ten Brink HJ, Schuit RC, and Jakobs C (2001) Journal of Lipid Research 42 9-16.

By essentially the same procedure antipyrine and Intercain (dimethylaminoethyl ester of /)-butyIaminobenzoic acid hydro-chloride)< > were determined. The attack by nitrous acid is probably on the phenyl ring, but the reaction products, which show a polarographic reduction wave, were not identified. 

Johnson, D.W., A rapid screening procedure for the diagnosis of peroxisomal disorders Quantification of very long-chain fatty acids, as dimethylaminoethyl esters, in plasma and blood spots, by electrospray tandem mass spectrometry. J. Inherit. Metab. Dis., 23, 475-486 (2000). 

Dimethylaminoethyl ester Animal growth-promoting substance, tuberculostatic. Light-yellow oil. Bpo 2 163°. 

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