Efficient, chemoenzymatic process for manufacture of the boceprevir bicyclic [3.1.0]proline intermediate based on amine oxidase-catalyzed desymmetrization

Journal of the American Chemical Society

Volumn 134, Issue 14, 2012, Pages 6467-6472

  Li, Tao ^a,c   Liang, Jack ^b   Ambrogelly, Alexandre ^a   Brennan, Tim ^a,d   Gloor, Guy ^a,e   Huisman, Gjalt ^b   Lalonde, James ^b   Lekhal, Azzeddine ^a   Mijts, Ben ^b   Muley, Sheela ^b   Newman, Lisa ^b   Tobin, Matt ^b   Wong, George ^a   Zaks, Aleksey ^a,f   Zhang, Xiyun ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b Department of Biocatalyst Characterization and Design   (United States)

^c U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^d Hospira   (United States)

^e Chesilton LLC   (United States)

^f Akermin Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE SUBSTRATES; ASYMMETRIC SYNTHESIS; CLINICAL TRIAL; CODEXIS; DESYM-METRIZATION; DEVELOPMENT STAGES; DRUG CANDIDATES; HEPATITIS C; KEY PARTS; OXIDATIVE DESYMMETRIZATION; REACTION SEQUENCES; SCHERING PLOUGHS; STRECKER REACTIONS; STRUCTURAL FEATURE;

AMINO ACIDS; DRUG THERAPY;

ORGANIC COMPOUNDS;

AMINE OXIDASE (FLAVIN CONTAINING); BOCEPREVIR; FUNGAL ENZYME; PROLINE DERIVATIVE;

ARTICLE; ASPERGILLUS NIGER; ASPERGILLUS ORYZAE; BIOCATALYSIS; CHEMICAL REACTION; CHEMOENZYMATIC ASYMMETRIC SYNTHESIS; CHIRALITY; CONCENTRATION (PARAMETERS); CRYSTAL STRUCTURE; DRUG MANUFACTURE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME CHEMISTRY; ENZYME INHIBITION; ENZYME KINETICS; MOLECULAR WEIGHT; NONHUMAN; OXIDATION; POLYMERASE CHAIN REACTION; REACTION OPTIMIZATION; SOLUBILITY; STRECKER SYNTHESIS; SULFONATION;

ANTIVIRAL AGENTS; CATALYSIS; CATALYTIC DOMAIN; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HEPATITIS C; HUMANS; KINETICS; MONOAMINE OXIDASE; OXYGEN; PROLINE; REPRODUCIBILITY OF RESULTS; TEMPERATURE;

EID: 84859594005     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3010495     Document Type: Article

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