Chem. Pharm. Bull.

Chem. Pharm. Bull., 52(4),470-472, April 2004

Notes

Preparation of Weinreb Amides Using 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride (DMT-MM)

Kazuhito HIOKI,^a,b Hiroko KOBAYASHI,^a Rumi OHKIHARA,^a Shohei TANI,^a,b and Munetaka KUNISHIMA^*^,a,b

^a Faculty of Pharmaceutical Sciences, Kobe Gakuin University; and ^b High Technology Research Center, Kobe Gakuin University; Nishi-ku, Kobe 651-2180, Japan. * To whom correspondence should be addressed. e-mail: kunisima@pharm.kobegakuin.ac.jp

Weinreb amides were successfully prepared from the corresponding carboxylic acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) in the solvents, methanol, isopropyl alcohol, and acetonitrile, which can solubilize DMT-MM. A variety of carboxylic acids were converted to the corresponding Weinreb amides in excellent yields by simply mixing with DMT-MM and N,O-dimethylhydroxylamine hydrochloride.

Key words Weinreb amide; dehydrating condensation; polar solvent; carboxylic acid

Notes

Preparation of Weinreb Amides Using 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride (DMT-MM)

Kazuhito HIOKI,a,b Hiroko KOBAYASHI,a Rumi OHKIHARA,a Shohei TANI,a,b and Munetaka KUNISHIMA*,a,b

a Faculty of Pharmaceutical Sciences, Kobe Gakuin University; and b High Technology Research Center, Kobe Gakuin University; Nishi-ku, Kobe 651-2180, Japan. * To whom correspondence should be addressed. e-mail: kunisima@pharm.kobegakuin.ac.jp

Kazuhito HIOKI,^a,b Hiroko KOBAYASHI,^a Rumi OHKIHARA,^a Shohei TANI,^a,b and Munetaka KUNISHIMA^*^,a,b

^a Faculty of Pharmaceutical Sciences, Kobe Gakuin University; and ^b High Technology Research Center, Kobe Gakuin University; Nishi-ku, Kobe 651-2180, Japan. * To whom correspondence should be addressed. e-mail: kunisima@pharm.kobegakuin.ac.jp