The synthesis of 2-(4-amino-5-chloro-2-methoxybenzamido) acetic acid 2, a metabolite of metoclopramide 1, has been accomplished through the coupling of 4-amino-5-chloro-2-methoxybenzoic acid 4 with glycine benzyl ester followed by a catalytic hydrogenation. Such a metabolite could not be detected directly in the human urines but only after its transformation into the corresponding methyl ester 6. Compound 6 was prepared both by condensing acid 4 with glycine methyl ester and by reacting acid 2 with diazomethane. HPLC analyses of biological samples were therefore performed after treatment with diazomethane. In five healthy volunteers, the percentage of 6 spanned the range 0.6-1.2\%.
SYNTHESIS OF A METABOLITE OF METOCLOPRAMIDE AND ITS DETECTION IN HUMAN URINE / V. Maurich, M. De Amici, C. De Micheli. - In: IL FARMACO. - ISSN 0014-827X. - 49:12(1994), pp. 805-808.
SYNTHESIS OF A METABOLITE OF METOCLOPRAMIDE AND ITS DETECTION IN HUMAN URINE
M. De AmiciSecondo
;C. De MicheliUltimo
1994
Abstract
The synthesis of 2-(4-amino-5-chloro-2-methoxybenzamido) acetic acid 2, a metabolite of metoclopramide 1, has been accomplished through the coupling of 4-amino-5-chloro-2-methoxybenzoic acid 4 with glycine benzyl ester followed by a catalytic hydrogenation. Such a metabolite could not be detected directly in the human urines but only after its transformation into the corresponding methyl ester 6. Compound 6 was prepared both by condensing acid 4 with glycine methyl ester and by reacting acid 2 with diazomethane. HPLC analyses of biological samples were therefore performed after treatment with diazomethane. In five healthy volunteers, the percentage of 6 spanned the range 0.6-1.2\%.
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