Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 21, Pages 7107-7111Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo101159a
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- Conacyt, Mexico [60366-Q, 22211]
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The reactivity of N-tert-butyloxycarbonyl-N-carboxyanhydrides derived from beta-alanine, (S)-beta(3-)homophenylglycine, and (S)-beta(3)-carboxyhomoglycine with different alpha- and beta-amino ester hydrochlorides was examined under ball-milling activation. In particular, good to excellent yields of several relevant alpha,beta- and beta,beta-dipeptides were obtained. An illustrative application of this methodology consisted in the high-yield synthesis of the mammalian alpha,beta-dipeptide N-Boc-L-carnosine-OMe.
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