Transformations of penicillin. Part III. A new route to 2,2-dimethyl-6β-phenylacetamidopenam-3α-ol S-oxide and its esters; o-nitrobenzoate as a protecting group for alcohols and phenols

Autor:	Ian Harold Coates, Peter G. Sammes, Derek H. R. Barton
Rok vydání:	1973
Předmět:	Sodium borohydride chemistry.chemical_compound Aqueous solution chemistry Decarboxylation Organic chemistry Alcohol Ammonium chloride Phenols Protecting group Tetrahydrofuran
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :599-603
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19730000599
Popis:	Esters of the title compound have been obtained by rearrangement of aroyl penicillanoyl peroxides, followed by decarboxylation. Certain of the aroyl esters so produced have been epimerised at position 6 with selected secondary amines. Conditions for the liberation of the title alcohol from some of its aroyl esters have been established. Thus, the 2,4-dinitrobenzoate can either be photohydrolysed, by irradiation in aqueous tetrahydrofuran, or reduced with sodium borohydride. o-Nitrobenzoate is a potentially useful protecting group for alcohols and phenols since the group can be removed in high yield by reduction with zinc dust and ammonium chloride; the alcohol is liberated with formation of 2,1-benzisoxazolin-3-one. In this manner the title alcohol was obtained from its o-nitrobenzoate in 95% yield.
Databáze:	OpenAIRE
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