An expedient, chemoselectiveN-chloroacetylation of aminoalcohols under metal-free bio-compatible conditions

Abstract

We are reporting for the first time, efficient, highly chemoselective N-chloroacetylation of amino compounds (amino alcohols, amino acids) by chloroacetyl chloride, without compromising its high reactivity, to give chloroacetamides in phosphate buffer within 20 min. We have systematically studied the effects of buffers, metal salts and HCl scavengers to optimize the reaction conditions. We have carried out intermolecular competitive reactions and shown that anilines and aliphatic amines can be selectively N-chloroacylated in the presence of alcohols and phenols. The acylated products are obtained in high yields and can be easily isolated without chromatographic separation. This reaction represents the first example of a metal-free biocompatible synthesis under neutral conditions. This method is eco-friendly, easily scalable and robust. We have further studied the intramolecular competitive reactions of aminoalcohols and prepared various N-chloroacetamides in very good yields. Finally, this protocol was conveniently extended to ceramides synthesis as well.

A Quenched Fluorescence‐based Assay for Selective Detection of Nitroaromatic Compounds using Pyrene‐Appended Oxacalix[4]arene Host

“…di-hydroxyoxacalix [4]arene (1, DHOC) and pyren-1-yl-methyl 2-chloroacetate (2, PMCA) were synthesized in accordance with the method described in the cited literature. [30,31] Data pertaining to the comprehensive synthesis as well as the characterization are included in the ESI (Section S1&S2, Scheme S1&S2, Figure S1-S6).…”