Synthesis of 1,3-diacylaminopropan-2-ols and corresponding 2-acyl derivatives as amide isosteres of natural lipids.
(1991) Chemistry and Physics of Lipids — Vol. 59, n° 3, p. 267-272 (1991)
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- N,N'-diacyl-1,3-diaminopropan-2-ols as amide isosteres of 1,3-diacylglycerols are obtained in 50-79% yields by treatment of 1,3-diaminopropan-2-ol with acid chlorides either in ether or THF in the presence of triethylamine and catalytic amounts of 4-dimethyl-aminopyridine. Subsequent acylation of the secondary alcohol function with a variety of carboxylic acids (e.g. fatty acids, N-protected amino acids, drug compounds) can be effected by various techniques (i.e. acid chlorides, symmetrical anhydrides, isopropenyl chloroformate) with yields ranging from 56% to 76%.
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Mergen, F., Lambert, D., Poupaert, J., Bidaine, A., & Dumont, P. (1991). Synthesis of 1,3-diacylaminopropan-2-ols and corresponding 2-acyl derivatives as amide isosteres of natural lipids. Chemistry and Physics of Lipids, 59(3), 267-272. https://doi.org/10.1016/0009-3084(91)90027-9 (Original work published 1991)