Erratum: Highly efficient asymmetric synthesis of sitagliptin (Journal of the American Chemical Society (2009) 131:25 (8798-8804) DOI: 10.1021/ja902462q);Highly efficient asymmetric synthesis of sitagliptin

Journal of the American Chemical Society

Volumn 131, Issue 25, 2009, Pages 8798-8804

  Hansen, Karl B ^a   Hsiao, Yi ^a   Xu, Feng ^a   Rivera, Nelo ^a   Clausen, Andrew ^a   Kubryk, Michele ^a   Krska, Shane ^a   Rosner, Thorsten ^a   Simmons, Bryon ^a   Balsells, Jaume ^a   Ikemoto, Nori ^a   Sun, Yongkui ^a   Spindler, Felix ^b   Malan, Christophe ^b   Grabowski, Edward J J ^a   Armstrong III, Joseph D ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b SOLVIAS AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

COST EFFECTIVENESS; RHODIUM COMPOUNDS;

ASYMMETRIC SYNTHESIS; CHEMICAL PURITY; COST EFFECTIVE; EFFICIENT SYNTHESIS; ENANTIOSELECTIVE HYDROGENATION; ISOLATED YIELD; PHOSPHATE SALTS; TYPE 2 DIABETES MELLITUS;

DRUG PRODUCTS;

PHOSPHATE; SITAGLIPTIN;

ARTICLE; ASYMMETRIC SYNTHESIS; CONTROLLED STUDY; DRUG ISOLATION; DRUG MANUFACTURE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HYDROGENATION; ISOLATION PROCEDURE; NON INSULIN DEPENDENT DIABETES MELLITUS; ONE POT SYNTHESIS;

EID: 67649583302     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.0c06041     Document Type: Erratum

References (33)

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26. Meldrum adduct 12, with a pKa of 3.1 as measured by titration in water at ambient temperature, is not stable in solution as its free acid. However, the anion of 12, which could be formed with Hunig's base, is quite stable.
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28. In collaboration with Solvias AG, Switzerland, extensive screenings were carried out to search for the most suitable catalyst for this hydrogenation.
29. 3 L/mol.
30. Optimal performance was achieved with a mole ratio of 1:1 NH4Cl/ catalyst.
31. For these experiments, no additional NH4Cl was added and the enamine 9 was purified through recrystalliztion. The observed acid additive effects on the reaction rate were clearly confirmed with controlled experiments by using the same lot of enamine 9 in the absences of acid additives.
32. Commercial source of Ecosorb C-941: Graver Technologies, Glasgow, DE 19702.
33. The Fe and Rh residue in the isolated sitagliptin free base is typically <20 ppm.