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Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives

Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives
Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives
A pilot-scale process has been developed for green and scalable synthesis of (±)-?-(3,4-dihydroxyphenyl) lactic acid ((±)-DSS) and their two important derivatives, namely, (±)-IDHP [(±)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate] and (±)-DBZ [(±)-bornyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate]. Subsequent hydrogenation has been carried out by employing Raney Ni as catalyst. The improved process results in higher yields of 47.5% for (±)-DBZ and 49.2% for (±)-IDHP compared to the initial process with a yield of 12% for (±)-DBZ and 18% for (±)-IDHP in our original medicinal chemistry route. Furthermore, kilograms of optical DBZ [(?)-S-DBZ and (+)-R-DBZ, >99% ee] and IDHP [(?)-S-IDHP and (+)-R-IDHP, >99% ee] have been produced by chiral high-performance liquid chromatography in good yield (>84%).
1667-1673
Bai, Yajun
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Zhang, Qunzheng
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Jia, Pu
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Yang, Lingjian
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Sun, Yuhong
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Nan, Yefei
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Wang, Shixiang
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Meng, Xue
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Wu, Yizhen
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Qin, Fanggang
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Sun, Zhe
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Gao, Xiaokang
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Liu, Pei
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Luo, Kai
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Zhang, Yajun
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Zhao, Xinfeng
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Xiao, Chaoni
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Liao, Sha
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Liu, Jianli
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Wang, Cuiling
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Fang, Jiacheng
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Wang, Xiaoxiao
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Wang, Jing
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Gao, Rong
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An, Xuexia
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Zhang, Xunli
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Zheng, Xiaohui
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Bai, Yajun
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Zhang, Qunzheng
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Jia, Pu
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Yang, Lingjian
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Sun, Yuhong
3805c192-a52d-4028-b264-8ec7fe603214
Nan, Yefei
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Wang, Shixiang
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Meng, Xue
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Wu, Yizhen
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Qin, Fanggang
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Sun, Zhe
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Gao, Xiaokang
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Liu, Pei
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Luo, Kai
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Zhang, Yajun
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Zhao, Xinfeng
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Xiao, Chaoni
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Liao, Sha
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Liu, Jianli
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Wang, Cuiling
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Fang, Jiacheng
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Wang, Xiaoxiao
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Wang, Jing
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Gao, Rong
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An, Xuexia
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Zhang, Xunli
d7cf1181-3276-4da1-9150-e212b333abb1
Zheng, Xiaohui
a42fbf32-c855-4ae7-adc1-e56debcc1ecc

Bai, Yajun, Zhang, Qunzheng, Jia, Pu, Yang, Lingjian, Sun, Yuhong, Nan, Yefei, Wang, Shixiang, Meng, Xue, Wu, Yizhen, Qin, Fanggang, Sun, Zhe, Gao, Xiaokang, Liu, Pei, Luo, Kai, Zhang, Yajun, Zhao, Xinfeng, Xiao, Chaoni, Liao, Sha, Liu, Jianli, Wang, Cuiling, Fang, Jiacheng, Wang, Xiaoxiao, Wang, Jing, Gao, Rong, An, Xuexia, Zhang, Xunli and Zheng, Xiaohui (2014) Improved process for pilot-scale synthesis of danshensu ((±)-DSS) and its enantiomer derivatives. Organic Process Research & Development, 18 (12), 1667-1673. (doi:10.1021/op4002593).

Record type: Article

Abstract

A pilot-scale process has been developed for green and scalable synthesis of (±)-?-(3,4-dihydroxyphenyl) lactic acid ((±)-DSS) and their two important derivatives, namely, (±)-IDHP [(±)-isopropyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate] and (±)-DBZ [(±)-bornyl 2-hydroxy-3-(3,4-dihydroxyphenyl)propanoate]. Subsequent hydrogenation has been carried out by employing Raney Ni as catalyst. The improved process results in higher yields of 47.5% for (±)-DBZ and 49.2% for (±)-IDHP compared to the initial process with a yield of 12% for (±)-DBZ and 18% for (±)-IDHP in our original medicinal chemistry route. Furthermore, kilograms of optical DBZ [(?)-S-DBZ and (+)-R-DBZ, >99% ee] and IDHP [(?)-S-IDHP and (+)-R-IDHP, >99% ee] have been produced by chiral high-performance liquid chromatography in good yield (>84%).

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Published date: 26 November 2014
Organisations: Bioengineering Group

Identifiers

Local EPrints ID: 372871
URI: http://eprints.soton.ac.uk/id/eprint/372871
PURE UUID: 140b5cb3-735e-4a9f-9749-f3b9e60ddc46
ORCID for Xunli Zhang: ORCID iD orcid.org/0000-0002-4375-1571

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Date deposited: 24 Dec 2014 12:21
Last modified: 15 Mar 2024 03:29

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Contributors

Author: Yajun Bai
Author: Qunzheng Zhang
Author: Pu Jia
Author: Lingjian Yang
Author: Yuhong Sun
Author: Yefei Nan
Author: Shixiang Wang
Author: Xue Meng
Author: Yizhen Wu
Author: Fanggang Qin
Author: Zhe Sun
Author: Xiaokang Gao
Author: Pei Liu
Author: Kai Luo
Author: Yajun Zhang
Author: Xinfeng Zhao
Author: Chaoni Xiao
Author: Sha Liao
Author: Jianli Liu
Author: Cuiling Wang
Author: Jiacheng Fang
Author: Xiaoxiao Wang
Author: Jing Wang
Author: Rong Gao
Author: Xuexia An
Author: Xunli Zhang ORCID iD
Author: Xiaohui Zheng

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