摘要
以乙醇-d6为原料,与碘反应得到碘乙烷-d_5,进一步与1-Boc-哌嗪经过两步反应得到中间体1-乙基哌嗪-d_5,然后与1-环丙基-7-氯-6-氟-1,4-二氢-4-氧代喹啉-3-羧酸乙酯发生Buchwald-Hartwig偶联反应得到1-环丙基-6-氟-1,4-二氢-4-氧-7-(4-乙基-1-哌嗪基)-3-喹啉羧酸乙酯-d_5,最后经碱水解后得到标题化合物,5步总收率为52%,其结构经1HNMR、13CNMR、IR与ESI-MS表征,化学纯度为99. 5%,同位素丰度为99. 3%,可作为食品安全领域检测用稳定同位素内标试剂。
The synthesis of enrofloxacin-d_5 has been achieved in five steps as follows: iodination of CD_3CD_2OD with I_2 to yield CD_3CD_2I,which was used to ethylation of 1-Boc-piperazine in 2 steps provided 1-ethylpiperazine-d_5.The key ethyl 1-cyclopropyl-7-( 4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate-d_5 was constructed from 1-ethylpiperazine-d_5 and ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate via a Buchwald-Hartwig coupling reaction. The final step was a hydrolyzation by alkaline.The total yield was 52%,and the structure was confirmed by1 HNMR,13 CNMR,IR and ESI-MS.The purity was 99. 5% and isotopic enrichment of D was 99. 3%.It could be used as an internal standard in the field of food safety detection.
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