- Stable isotope deuterium labeled sulfanilamide drug and preparation method thereof
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The invention belongs to the technical field of chemical synthesis, and specifically relates to a stable isotope deuterium labeled sulfanilamide drug and a preparation method thereof. The preparationmethod comprises the following steps: (1) subjecting benzene-d6 (I) to a nitratlon reaction so as to prepare deuterium labeled nitrobenzene-d5 (II); (2) reducing nitro of the deuterium labeled nitrobenzene-d5 (II) so as to prepare deuterium labeled aniline-d5 (III); (3) under the conditions of anhydrous sodium acetate and glacial acetic acid, subjecting the deuterium labeled aniline-d5 (III) and acetic anhydride to a reaction so as to prepare deuterium labeled N-acetanilide-d5 (IV); (4) subjecting the deuterium labeled N-acetanilide-d5 (IV) and chlorosulfonic acid to a reaction so as to prepare deuterium labeled 1-chlorosulfonyl-4-acetamidobenzene-d4 (V); and (5) allowing R to substitute chlorine of the deuterium labeled 1-chlorosulfonyl-4-acetamidobenzene-d4 (V), and carrying out hydrolysis so as to prepare an isotope deuterium labeled sulfanilamide drug (VII). The preparation method provided by the invention has the advantages of simple reaction conditions, short reaction time, highconversion efficiency, strong economy, and applicability to mass synthesis.
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- General method of obtaining deuterium-labeled heterocyclic compounds using neutral D2O with heterogeneous Pd/C
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A protocol of a versatile H-D exchange reaction of heterocyclic compounds catalyzed by heterogeneous Pd/C in D2O is described. The reaction of various nitrogen-containing heterocycles with 10% Pd/C (10 wt % of the substrate) under hydrogen atmosphere in D2O as a deuterium source at 110-180 °C for 24 h afforded the corresponding deuterated compounds with satisfactory efficiency of deuteration in moderate to excellent isolated yields. Furthermore, the Pd/C-H2-D2O system can be extended to the direct deuteration of biologically active compounds such as sulfamethazine, which is used as a synthetic antibacterial drug for fat stocks and would be applied as a general method for the preparation of the standard materials for the analysis of residual chemicals in foods and so on.
- Esaki, Hiroyoshi,Ito, Nobuhiro,Sakai, Shino,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
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p. 10954 - 10961
(2007/10/03)
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