An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh₃

Duangkamol, Chuthamat; Jaita, Subin; Wangngae, Sirilak; Phakhodee, Wong; Pattarawarapan, Mookda

An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh₃

2015

Duangkamol, Chuthamat | Jaita, Subin | Wangngae, Sirilak | Phakhodee, Wong | Pattarawarapan, Mookda

A rapid, facile, and efficient mechanochemical synthesis of amides from carboxylic acids has been developed through an in situ acid activation with 2,4,6-trichloro-1,3,5-triazine and a catalytic amount of PPh₃. Under room temperature solvent-drop grinding of the reactants in the presence of an inorganic base, a variety of carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids undergo amidation to afford amides in moderate to excellent yields. The method is also compatible with Fmoc, Cbz, and Boc protecting groups which yields protected optically active dipeptides without detectable racemization.

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