Lipase-Catalyzed Regioselective Ester Hydrolysis as a Key Step in an Alternative Synthesis of a Buprenorphine Pro-Drug,Organic Process Research & Development

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Lipase-Catalyzed Regioselective Ester Hydrolysis as a Key Step in an Alternative Synthesis of a Buprenorphine Pro-Drug
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2019-04-18 00:00:00 , DOI: 10.1021/acs.oprd.9b00026
John S. Carey ₁ , Emily McCann ₁

Affiliation

This paper describes the development of an alternative route toward a hemiadipic acid pro-drug of buprenorphine. Buprenorphine was acylated with adipic acid monoethyl ester. A regioselective ester hydrolysis using C. antarctica lipase B cleaved the sterically less-hindered alkyl ester in the presence of the more labile phenolic ester. In this manner the pro-drug could be isolated in good yield and high purity.

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