Chemoenzymatic synthesis of the calcimimetics (+)-NPS R-568 via asymmetric reductive acylation of ketoxime intermediate

Tetrahedron Letters

Volumn 51, Issue 27, 2010, Pages 3536-3537

  Han, Kiwon ^a   Kim, Yunwoong ^a   Park, Jaiwook ^a   Kim, Mahn Joo ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

3' METHOXYACETOPHENONE; ACETOPHENONE DERIVATIVE; CALCIMIMETIC AGENT; N [3 (2 CHLOROPHENYL)PROPYL] 1 (3 METHOXYPHENYL)ETHYLAMINE; PALLADIUM; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; REDUCTION;

EID: 77954244523     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.121     Document Type: Article

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28. 1H NMR spectroscopy and HPLC (Whelk-O1, n-hexane/2-propanol = 80/20, flow rate = 0.50 mL/min, UV 217 nm). The separated catalysts were washed with ethyl acetate, dried in vacuo, and then reused for next run.
29. The catalysts were reused several times without losing any significant activity in the dynamic kinetic resolution of primary amines. See Ref. 5f.
30. 16
31. +), found 151.1001. The % ee was determined by HPLC after converting to the corresponding amide by treatment with a few drops of methoxyacetyl chloride.
32. 3 in methanol under 1 bar of molecular hydrogen.
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34. It is noted that the direct synthesis of 6 from 3 using 3-(2-chlorophenyl)-propionic acid ethyl ester as the acyl donor in the asymmetric reductive acylation was unsuccessful because CALB (Novozym 435) was unreactive toward the ester.
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