Stereochemical Studies. XVII. Nitrous Acid Deaminations of (R)-α-Methylphenylalanine and Its Methyl Ester in Acetic Acid

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概要

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• Detailed examinations on nitrous acid deamination of (R)-α-methylphenylalanine methyl ester (I) in acctic acid have shown that elimination (68%), substitution (21%), hydrogen migration (8%), and phenyl migration (3%) products were obtained. The stereochemical courses of these products were also clarified. Substitution reactions giving α-hydroxy ester (VIII) and α-acetoxy ester (IX) proceeded with net retention, while migration reactions proceeded with net inversion at their migration termini, as shown in Table I. Nitrous acid deamination of (R)-α-methylphenylalanine (II) in acetic acid was also examined as shown in Table II.

• 公益社団法人日本薬学会の論文
• 1972-09-25

著者

• 山田 俊一

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 古賀 憲司

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 小林 通洋

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)research Laboratory Kissei P

• Koga Kenjiro

  Department Of Pharmaceutics Faculty Of Pharmaceutical Sciences Hokuriku University

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