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Beilstein Journal of Organic Chemistry

Beilstein Journal of Organic Chemistry

IF: 2.2
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Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid.

Published:21 April 2020 DOI: 10.3762/bjoc.16.73 PMID: 32395183
Dong Cai, ZhiHua Zhang, Yufan Meng, KaiLi Zhu, LiYi Chen, ChangXiang Yu, ChangWei Yu, ZiYi Fu, DianShen Yang, YiXia Gong

Abstract

In the present study, a practical method to prepare piperazinyl amides of 18β-glycyrrhetinic acid was developed. Two main procedures for the construction of important intermediate 8 are discussed. One procedure involves the amidation of 1-Boc-piperazine with 3-acetyl-18β-glycyrrhetinic acid, prepared by the reaction of 18β-glycyrrhetinic acid with acetic anhydride without any solvent at 130 °C. The other procedure to prepare compound 8 involves the amidation of 18β-glycyrrhetinic acid followed by the esterification with acetic anhydride. Finally, compound 8 underwent N-Boc deprotection to prepare product 4. To ascertain the scope of the reaction, another C-3 ester derivative 17 was tested under the optimized reaction conditions. Furthermore, the reasons for the appearance of byproducts were elucidated. Crystallographic data of a selected piperazinyl amide is reported.

Substances (6)

Related products
Procduct Name CAS Molecular Formula Supplier Price
1-BOC-Piperazine 57260-71-6 C9H18N2O2 847 suppliers $5.00-$12970.00
18β-Glycyrrhetinic Acid 471-53-4 C30H46O4 602 suppliers $19.80-$3176.25
1-Boc-Pyrrolidine 86953-79-9 C9H17NO2 219 suppliers $9.00-$5058.90
1-BOC-PIPERAZINE 57260-72-7 C11H20N2O6 158 suppliers Inquiry
2-[1-(4-PIPERONYL)PIPERAZINYL] BENZOTHIAZOLE C19H19N3O2S 14 suppliers Inquiry
Chenodeoxycholic Acid, Free Acid 5 suppliers Inquiry

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