Method for synthesizing novel chiral ligand, metal chelate, a variety of non-natural amino acids, maraviroc and key intermediate thereof

US10875883B2 · kind B2 · utility

Assignee

• SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES · CN

Inventors

• Hong Liu · Shanghai, CN
• Jiang Wang · Shanghai, CN
• Shengbin Zhou · Shanghai, CN
• Panfeng Peng · Shanghai, CN
• Yong Nian · Shanghai, CN
• Shuni Wang · Shanghai, CN
• Shuangjie Shu · Shanghai, CN
• Hao Shen · New York, US
• Hualiang Jiang · Shanghai, CN
• Kaixian Chen · Shanghai, CN

Key dates

• Filing date: Sep 19, 2017
• Grant date: Dec 29, 2020
• Expiry date: Sep 19, 2037

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Disclosed is a method for synthesizing a novel chiral ligand, a metal chelate, a variety of non-natural amino acids, Maraviroc and a key intermediate thereof. In the invention, (R)-2-methyl proline is selected and used as a starting raw material, (S)-β3-amino acid is obtained by asymmetric resolution induced by using a nickel chelate, and Maraviroc is synthesized by using (S)-3-amino-3-phenylpropionic acid as a key intermediate with a high yield and the ee value reaching 98.2% or more. The method of the present invention has widely available materials, mild synthetic process conditions, is easy to control, and produces a product of a high optical purity.