Optical Resolution and Optimization of (R, S)‐Propranolol Using Dehydroabietic Acid Via Diastereomeric Crystallization. Issue 2 (29th October 2014)

• Record Type: Journal Article
• Authors: Ge, Li; Zhao, Qiongqiong; Yang, Kedi; Liu, Shishi; Xia, Fan
• Is Part Of: Chirality. Volume 27:Issue 2(2015)
• Page Start: 131
• Page End: 136
• Publication Date: 2014-10-29
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22401
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <p>The optical resolution of (<italic>R</italic>, <italic>S</italic>)‐propranolol by the diastereomeric crystallization method was successfully performed using dehydroabietic acid (DHAA) as the resolving agent in methanol. The three important parameters: DHAA amount, solvent (methanol) amount, and crystallization temperature of diastereomeric salts were optimized employing the response surface methodology (RSM). When maintaining a lower limit of 95% for the purity of (<italic>S</italic>)‐propranolol, the optimal resolution conditions were a DHAA/(<italic>R</italic>, <italic>S</italic>)‐propranolol molar ratio of 1.1, solvent/(<italic>R</italic>, <italic>S</italic>)‐propranolol ratio of 16.2 mL.g^‐1, and crystallization temperature of –5 °C. The desired (<italic>S</italic>)‐propranolol was prepared with 94.8% optical purity and 72.2% yield under the optimal conditions. <italic>Chirality 27:131–136, 2015</italic>. © 2014 Wiley Periodicals, Inc.</p> </abstract>