| pubmed-article:19140725 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:19140725 | lifeskim:mentions | umls-concept:C0284930 | lld:lifeskim |
| pubmed-article:19140725 | lifeskim:mentions | umls-concept:C0012727 | lld:lifeskim |
| pubmed-article:19140725 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:19140725 | lifeskim:mentions | umls-concept:C1999216 | lld:lifeskim |
| pubmed-article:19140725 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:19140725 | lifeskim:mentions | umls-concept:C2351970 | lld:lifeskim |
| pubmed-article:19140725 | pubmed:issue | 4 | lld:pubmed |
| pubmed-article:19140725 | pubmed:dateCreated | 2009-2-20 | lld:pubmed |
| pubmed-article:19140725 | pubmed:abstractText | An enantioselective synthesis of the Cathepsin K inhibitor odanacatib (MK-0822) 1 is described. The key step involves the novel stereospecific S(N)2 triflate displacement of a chiral alpha-trifluoromethylbenzyl triflate 9a with (S)-gamma-fluoroleucine ethyl ester 3 to generate the required alpha-trifluoromethylbenzyl amino stereocenter. The triflate displacement is achieved in high yield (95%) and minimal loss of stereochemistry. The overall synthesis of 1 is completed in 6 steps in 61% overall yield. | lld:pubmed |
| pubmed-article:19140725 | pubmed:language | eng | lld:pubmed |
| pubmed-article:19140725 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19140725 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:19140725 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19140725 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19140725 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19140725 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19140725 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19140725 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19140725 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19140725 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19140725 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19140725 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:19140725 | pubmed:month | Feb | lld:pubmed |
| pubmed-article:19140725 | pubmed:issn | 1520-6904 | lld:pubmed |
| pubmed-article:19140725 | pubmed:author | pubmed-author:ChenCheng-yiC... | lld:pubmed |
| pubmed-article:19140725 | pubmed:author | pubmed-author:VolanteRalph... | lld:pubmed |
| pubmed-article:19140725 | pubmed:author | pubmed-author:GosselinFranc... | lld:pubmed |
| pubmed-article:19140725 | pubmed:author | pubmed-author:O'SheaPaul... | lld:pubmed |
| pubmed-article:19140725 | pubmed:author | pubmed-author:GauvreauDanny... | lld:pubmed |
| pubmed-article:19140725 | pubmed:author | pubmed-author:NadeauChristi... | lld:pubmed |
| pubmed-article:19140725 | pubmed:author | pubmed-author:HughesGregG | lld:pubmed |
| pubmed-article:19140725 | pubmed:issnType | Electronic | lld:pubmed |
| pubmed-article:19140725 | pubmed:day | 20 | lld:pubmed |
| pubmed-article:19140725 | pubmed:volume | 74 | lld:pubmed |
| pubmed-article:19140725 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:19140725 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:19140725 | pubmed:pagination | 1605-10 | lld:pubmed |
| pubmed-article:19140725 | pubmed:dateRevised | 2009-11-19 | lld:pubmed |
| pubmed-article:19140725 | pubmed:meshHeading | pubmed-meshheading:19140725... | lld:pubmed |
| pubmed-article:19140725 | pubmed:meshHeading | pubmed-meshheading:19140725... | lld:pubmed |
| pubmed-article:19140725 | pubmed:meshHeading | pubmed-meshheading:19140725... | lld:pubmed |
| pubmed-article:19140725 | pubmed:meshHeading | pubmed-meshheading:19140725... | lld:pubmed |
| pubmed-article:19140725 | pubmed:meshHeading | pubmed-meshheading:19140725... | lld:pubmed |
| pubmed-article:19140725 | pubmed:meshHeading | pubmed-meshheading:19140725... | lld:pubmed |
| pubmed-article:19140725 | pubmed:meshHeading | pubmed-meshheading:19140725... | lld:pubmed |
| pubmed-article:19140725 | pubmed:meshHeading | pubmed-meshheading:19140725... | lld:pubmed |
| pubmed-article:19140725 | pubmed:meshHeading | pubmed-meshheading:19140725... | lld:pubmed |
| pubmed-article:19140725 | pubmed:meshHeading | pubmed-meshheading:19140725... | lld:pubmed |
| pubmed-article:19140725 | pubmed:year | 2009 | lld:pubmed |
| pubmed-article:19140725 | pubmed:articleTitle | A practical enantioselective synthesis of odanacatib, a potent Cathepsin K inhibitor, via triflate displacement of an alpha-trifluoromethylbenzyl triflate. | lld:pubmed |
| pubmed-article:19140725 | pubmed:affiliation | Department of Process Research, Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe-Claire-Dorval, Québec, H9R 4P8, Canada. paul_oshea@merck.com | lld:pubmed |
| pubmed-article:19140725 | pubmed:publicationType | Journal Article | lld:pubmed |
