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Preparation of n amino n' tert butoxycarbonyl l proline esters and attempted cyclization into 1 oxa 4 5 diazepin 2 ones


, : Preparation of n amino n' tert butoxycarbonyl l proline esters and attempted cyclization into 1 oxa 4 5 diazepin 2 ones. Acta Pharmaceutica Jugoslavica 30(4): 183-188

A new N-amino-proline derivative, N-amino-(N'-tert-butoxy-carbonyl)-L-proline was prepared in .apprx. 60% yield. It was alkylated with .alpha.-halomethyl-aryl ketones to give benzoyl methyl esters 2-5. Attempts to obtain ring closure of hydrobromides (prepared by deprotection of 2-5 with 2.5% hydrobromic acid in acetic acid) into 1-oxa-4,5-diazepin-2-ones failed.

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Related references

Ihle, N.C..; Krause, A.E.., 1996: Preparation of 4-Alkyl-2-[N-(tert-butoxycarbonyl)amino]pyridines by Alkylation, Nucleophilic Addition, and Acylation of 2-[N-(tert-Butoxycarbonyl)amino]-4-picoline(1). Journal of Organic Chemistry 61(14): 4810-4811

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