Trapping carbamates of ?-Amino acids: One-Pot and catalyst-free synthesis of 5-Aryl-2-Oxazolidinonyl derivatives

Carbonation of natural ?-amino acids in water and subsequent cyclization with (2-bromo-1-arylethyl)dimethylsulfonium bromides led selectively to a family of 2-oxazolidinonyl derivatives, which were isolated without the needing of purification. Analogous conjugation of the 2-oxazolidinone skeleton with amino acids was previously realized by complicated and narrow-scope routes, whereby the amino acid core is built stepwise. Deprotonation of some of the products afforded the corresponding water-soluble carboxylates, while a straightforward, proof of concept esterification reaction of the carboxylic acid group yielded a menthol-alanineoxazolidinone conjugate.

Automated summary

By carbonation of natural α-amino acids in water and subsequent cyclization with (2-bromo-1-arylethyl)dimethylsulfonium bromides, a series of 2-oxazolidinonyl derivatives were selectively produced without the need for purification. This method offers a more straightforward and efficient way to synthesize water-soluble compounds compared to previous approaches, showing potential for further reactions.