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US 9,068,207 B2Granted
Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester
AssigneeSK Biopharmaceuticals Co., Ltd.
InventorsSang Chul Lim, Moo Yong Uhm, Dae Won Lee, Hui Ho Kim, Dong Ho Lee, Hyun Seok Lee
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Abstract
Disclosed is a method for the preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl esters, comprising the enantioselective enzyme reduction of a 1-aryl-2-tetrazolyl-ethyl ketone to form a (R)-1-aryl-2-tetrazolyl-ethyl alcohol and the carbamation of said alcohol.
Claims21
A method for preparing carbamic acid aryl-2-tetrazolyl ethyl ester of Chemical Formula 1, comprising:
- subjecting an arylketone of Chemical Formula 2, to enantioselective enzymatic reduction in a reaction mixture comprising said compound of Chemical Formula 2, an oxidoreductase having at least 90% homology with amino acid sequence SEQ ID NO:
- 4, NADH or NADPH as a cofactor that is oxidized during the reduction process and continuously regenerated, a second substrate comprising a secondary alcohol of the Formula RR′CHOH, wherein R and R′ are independent from one another and have from 1 to 10 carbon atoms, and a suitable buffer to form an alcohol compound of (R)-configuration of Chemical Formula 3;
- and
- carbamating said alcohol
- wherein,
- R1 and R2 are independently selected from the group consisting of hydrogen, halogen, perfluoroalkyl, an alkyl of 1 to 8 carbon atoms, a thioalkoxy of 1 to 8 carbon atoms, and an alkoxy of 1 to 8 carbon atoms;
- and
- one of A1 and A2 is CH with the other being N.
5 more elements
A method for preparing an alcohol compound of Chemical Formula 3, through the enantioselective enzymatic reduction of an arylketone of Chemical Formula 2:
- wherein,
- R1 and R2 are independently selected from a group consisting of hydrogen, halogen, perfluoroalkyl, an alkyl of 1 to 8 carbon atoms, a thioalkoxy of 1 to 8 carbon atoms, and an alkoxy of 1 to 8 carbon atoms,
- one of A1 and A2 is CH with the other being N;
- and
- said reduction is carried out in a reaction mixture comprising said compound of Chemical Formula 2, an oxidoreductase having at least 90% homology with amino acid sequences SEQ ID NO:4, NADH or NADPH as a cofactor that is oxidized during the reduction process and continuously regenerated, a second substrate comprising a secondary alcohol of the Formula RR′CHOH, wherein R and R′ are independent from one another and have from 1 to 10 carbon atoms, and a suitable buffer.
2 more elements
Dependencies are inferred from the claim text.