Structure Determination of By-product in Grignard Reaction for Preparing Mifepristone Derivatives

Abstract

Abstract: Aim To determine the structure of the by-product produced in Grignard reaction for preparing mifepristone derivatives, and elucidate the reaction mechanism. Methods The structure of the by-product was determined with elemental analysis, one- and two-dimension spectra NMR (DEPT, 1H-1Hcosy, HMQC, HMBC) and compared with those of mifepristone. Results The main by-product was 11,17-di-addition product of Grignard reagent of N, N-dimethylamino phenyl bromide. Conclusion This is the first complete assignment of ¹H NMR and ¹³C NMR of compound (3).

Key words: by-product identification, by-product identification, mifepristone deriva tives, mifepristone deriva tives, two-dimension NMR, two-dimension NMR

CLC Number:

R916.41

R917.02

Supporting:

CHEN An-ping, LEI Xiao-ping^* . Structure Determination of By-product in Grignard Reaction for Preparing Mifepristone Derivatives[J]. .

[1]	Chao Li, Ying Guo, Chao Tian, Shouxin Zhou, Rufeng Yan, Zhili Zhang, Xiaowei Wang, Junyi Liu^*. Expression, purification and activity assay of recombinant human thymidylate synthase [J]. , 2013, 22(2): 173-176.
[2]	Chao Tian, Zhi-Li Zhang, Jun-Yi Liu^* . Synthesis and evaluation of 8-deaza-5,6,7,8-tetrahydromethotrexate derivatives as dihydrofolate reductase inhibitors [J]. , 2012, 21(2): 142-148.
[3]	Jing-Qian Jiang, Zheng-Ren Xu, Yan-Xing Jia^*. CuI-catalyst N-arylation of 4-iodotryptophan derivatives: effort toward the total synthesis of indolactam V [J]. , 2012, 21(2): 113-123.
[4]	Liang-Liang Shi, Hai-Nan Wei, Chang-Mei Cheng^, Lang-Qiu Chen^, Yi-Gang Tong . Synthesis of telbivudine 3'-O-acetyl-5'-O-phenyl-N-alkylphosphramidates and evaluation of their anti-HBV activities [J]. , 2011, 20(5): 454-459.
[5]	Ai-Li Fan, Wen-Han Lin, Yan-Xing Jia^*. Recent progress in the research on lamellarins and related pyrrole-derived alkaloids from marine organisms [J]. , 2011, 20(5): 425-441.
[6]	Qing Li, Yue-Tao Zhao, Xiang-Bao Meng, Ting-Ting Yan, Shu-Chun Li, He-Qing Huang, Zhi-Hui Zhao^, Zhong-Jun Li^ . Synthesis of two multivalent lactosides with anti-adhesive activity and their fluorescein-labeled and biotin-labeled derivatives [J]. , 2011, 20(4): 325-334.
[7]	Rui Sun, Jing Song, Hui Zhao, Chun-Li Yan, Ai-Jun Zhang, Diwa Koirala, Da-Wei Li, Chun Hu^*. Synthesis and anti-tumor activity of 1,4-dihydrothieno[3',2':5,6]thiopyrano[4,3-c]pyrazole-3-carboxylic amide derivatives [J]. , 2011, 20(1): 32-36.
[8]	Gong Li, Qi Sun, Jing-Rong Cui, Run-Tao Li^. Modification of the alkylating agent chlorambucil with spiropiperazinium salts [J]. , 2010, 19(5): 346-352.
[9]	Yu Zheng, Xiang-Bao Meng, Shu-Chun Li, He-Qing Huang, Zhong-Jun Li^, Qing Li^ . Synthesis and anti-tumor activities of 5-carbohydrate modified cyclophosphamide derivates [J]. , 2010, 19(5): 327-340.
[10]	Rui-Juan Xing, Li Pan, Xi Wen, Jian Wang, Mao-Sheng Cheng^* . A practical and efficient procedure for the α-bromination of arylethanones [J]. , 2010, 19(5): 400-402.
[11]	Li Li, Hua Qin, Liang Zhang, Xiao-Wei Wang, Jun-Yi Liu^* . Study on the iodination of uracil derivatives [J]. , 2010, 19(2): 146-150.
[12]	Hao Zou, Hao Jiang, Jie-Yun Zhou, Yan Zhu^, Lin Cao, Peng Xia, Qian Zhang^ . Synthesis of 3-(4-hydroxyphenyl)-4-methyl-6-methoxy-7-hydroxycoumarin and its analogues as angiogenesis inhibitors [J]. , 2010, 19(2): 136-140.
[13]	Chang-Xin Huo, Xin-Shan Ye^* . Synthesis of S-linked tumor-associated carbohydrate antigen STn [J]. , 2009, 18(3): 214-217.
[14]	Wei-Wei He, Zhao-Fei Liu, Dan Liu, Bing Jia, Fan Wang^, Yu-Xin Cui^*. Preliminary in vitro biological evaluation of novel O⁶-benzylguanine derivative-precursors of PET tracers for the DNA repair protein AGT [J]. , 2008, 17(1): 70-74.
[15]	Yang Xu, Hua Yang, Jin Hu, Xiao-Wei Wang, Jun-Yi Liu^*. Study on the regioselective alkylation of 2-thiopyrimidine [J]. , 2007, 16(2): 125-127.

Structure Determination of By-product in Grignard Reaction for Preparing Mifepristone Derivatives

PDF (PC)

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments