The Preparation of Chenodeoxycholic Acid and Its Glycine and Taurine Conjugates.

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Abstract
The preparation of chenodeoxycholic acid is described in detail. 3[alpha], 7[alpha]-dihydroxy-12-keto-5[beta]-cholanic acid is prepared from cholic acid and reduced by the Huang-Minion modification of the Wolff-Kishner procedure. The crude acid is methylated and chromatographed on alumina using ethyl acetate-benzene mixtures as eluants. Small fractions are collected and examined by thin layer chromatography. Those fractions containing the pure methyl ester are pooled and saponified. The chromatographically pure acid crystallizes easily from ethyl acetate-heptane, m.p. 119[degree]. The net yield is 10[long dash]15%. The intermediates in the synthesis have been purified chromatographically; melting points and thin layer chromatographic behaviour are given. Methods for preparing sodium taurochenodeoxycholate and sodium glycochenode-oxycholate in a high state of purity are presented.