Publication: 3-(Dimethylamino)-2,2-dimethyl-2H-azirin als Aib-Äquivalent: Synthese von Aib-Oligopeptiden
3-(Dimethylamino)-2,2-dimethyl-2H-azirin als Aib-Äquivalent: Synthese von Aib-Oligopeptiden
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Obrecht, D., & Heimgartner, H. (1987). 3-(Dimethylamino)-2,2-dimethyl-2H-azirin als Aib-Äquivalent: Synthese von Aib-Oligopeptiden. Helvetica Chimica Acta, 70, 102–115. https://doi.org/10.1002/hlca.19870700112
Abstract
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Abstract
3-(Dimethylamino)-2,2-dimethyl-2H-azirine (1) reacts with carboxylic acids at 0-25° to give 2-acylamino-N,N,2-trimethylpropionamides (= 2-acylamino-N,N-dimethylisobutyramide, acyl-Aib-NMe2) in excellent yields (Scheme 2 and 3). Examples of alpha-amino-, alpha-hydroxy-, and alpha-mercapto-carboxylic acids are given. On treatment with HCI in toluene, the terminal dimethylamide group is selectively converted to the corresponding carboxylic acid (acyl-Aib) via an amide cleavage (Scheme 4 and 5); 1,3-oxazol-5(4H)-ones are intermediates of
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- Obrecht, Daniel
- Heimgartner, Heinz
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Obrecht, D., & Heimgartner, H. (1987). 3-(Dimethylamino)-2,2-dimethyl-2H-azirin als Aib-Äquivalent: Synthese von Aib-Oligopeptiden. Helvetica Chimica Acta, 70, 102–115. https://doi.org/10.1002/hlca.19870700112
