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Preparation of intermediates for uro porphyrin synthesis


Journal of Organic Chemistry 41(18): 2991-2994
Preparation of intermediates for uro porphyrin synthesis
The obtention of dipyrrylmethanes necessary for the synthesis of uroporphyrins III, IV and II (as octamethyl esters) is described. The necessary pyrroles were prepared by transesterification of the corresponding tribenzyl esters with methanol and sulfuric acid, which produced the transesterification of the side chain esters, but not of the nuclear benzyloxycarbonyl groups. The dimethyl esters of the 2-methyl-5-benzyloxycarbonylpyrroles thus obtained were converted into their 2-chloromethyl derivatives, which were condensed at 180.degree. C with the dimethyl esters of the 5-free 2-benzyloxycarbonylpyrroles. The tetramethyl esters of the 5,5'-dibenzyloxycarbonyldipyrrylmethanes thus prepared were converted by hydrogenolysis into the corresponding 5,5'-dicarboxydipyrrylmethanes, which were condensed with the tetramethyl ester of a 5,5'-diformyldiprrylmethane to afford the above-mentioned uroporphyrin esters. The 5,5'-free dipyrrylmethane necessary for the synthesis of the 5,5'-diformyldipyrrylmethane was obtained by hydrogenolysis of a 5,5'-dibenzyloxycarbonyldipyrrylmethane, decarboxylation with iodine of the resulting 5,5'-diacid, and reduction of the 5,5'-diiododipyrrylmethane with hydrogen.

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Accession: 006173330

PMID: 956947



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