Synthesis of carborane analogues of γ-aminobutanoic acid |
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Authors: | Valentina A Ol’shevskaya Rami Ayuob Pavel V Petrovskii Galina L Levit Valery N Charushin Valery N Kalinin |
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Institution: | a A.N. Nesmeyanov Institute of Organoelement Compounds of RAS, Vavilova St., 28, Moscow 119991, Russia b I.Ya. Postovsky Institute of Organic Synthesis of RAS (Ural Div.), S. Kovalevskoy St., 20, Ekaterinburg 620219, Russia |
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Abstract: | General method for preparation of high yields of novel N-protected carborane amino acid derivatives, 3-acylamino-1-carboxymethyl-2-R-o-carboranes (R = H, Me, Ph), is reported. The synthesis starts from readily available 3-amino-o-carboranes and includes the protection of amino group, introduction of carboxymethyl function to the carbon atom of polyhedron via the metallation of carborane CH bond with sodium amide in liquid ammonia, and treatment of corresponding sodium carboranes with sodium bromoacetate. Deprotection of N-acylated carborane amino acids is studied in acidic media. Depending on the procedure employed, closo- or nido-carborane amino acids were obtained. |
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Keywords: | 3-Amino-o-carboranes Amino acids Protection Deprotection Acidic hydrolysis |
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