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Volumn 76, Issue 4, 2011, Pages 1062-1071

Erratum: A practical synthesis of renin inhibitor MK-1597 (ACT-178882) via catalytic enantioselective hydrogenation and epimerization of piperidine intermediate (Journal of Organic Chemistry (2011) 76 (1062-1071) DOI: 10.1021/jo102070e);A practical synthesis of renin inhibitor MK-1597 (ACT-178882) via catalytic enantioselective hydrogenation and epimerization of piperidine intermediate

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; HYDROGENATION;

EID: 79951668329     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202488m     Document Type: Erratum
Times cited : (33)

References (48)
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    • Also known as ACT-178882.
    • Also known as ACT-178882.
  • 33
    • 79951646415 scopus 로고    scopus 로고
    • A% = HPLC area percent monitored at 220 nm.
    • A% = HPLC area percent monitored at 220 nm.
  • 34
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    • Other Pt-and Rh-based metals were also tested; however, much lower reactivities and/or purity profiles were observed.
    • Other Pt-and Rh-based metals were also tested; however, much lower reactivities and/or purity profiles were observed.
  • 35
    • 0034678241 scopus 로고    scopus 로고
    • 3·THF see:;, and references therein
    • 3·THF see: Kanth, J. V. B.; Brown, H. C. Inorg. Chem. 2000, 39, 1795 and references therein
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    • Kanth, J.V.B.1    Brown, H.C.2
  • 39
    • 38049047508 scopus 로고    scopus 로고
    • For a description of the microscale screening conditions utilized in this study see
    • For a description of the microscale screening conditions utilized in this study see: Shultz, C. S.; Krska, S. Acc. Chem. Res. 2007, 40, 1320
    • (2007) Acc. Chem. Res. , vol.40 , pp. 1320
    • Shultz, C.S.1    Krska, S.2
  • 41
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    • Process for the preparation of enantiomerically enriched cyclic β-aryl or heteroaryl carboxylic acids. U.S. Pat. Appl. 2007/0232653 A1, (2) resolution of the racemic carboxylic acid: ref 16a; (3) asymmetric hydrogenation on the carboxylic acid: ref 16b.
    • Bachmann, S.; Scalone, M.; Schnider, P. Process for the preparation of enantiomerically enriched cyclic β-aryl or heteroaryl carboxylic acids. U.S. Pat. Appl. 2007/0232653 A1, 2007; (2) resolution of the racemic carboxylic acid: ref 16a; (3) asymmetric hydrogenation on the carboxylic acid: ref 16b.
    • (2007)
    • Bachmann, S.1    Scalone, M.2    Schnider, P.3
  • 42
    • 79951644044 scopus 로고    scopus 로고
    • Other ligands tested: (S)-xyl-BINAP, (R, R)-Me-DuPhos, (R, R, S, S)-Tangphos, W006-1, Catasium I, J004-1 and J212-1 (structures are available in the Supporting Information)
    • Other ligands tested: (S)-xyl-BINAP, (R, R)-Me-DuPhos, (R, R, S, S)-Tangphos, W006-1, Catasium I, J004-1 and J212-1 (structures are available in the Supporting Information)
  • 43
    • 79951660067 scopus 로고    scopus 로고
    • The Darco treatment is necessary to reduce the metal content in the product. Before treatment the levels are >20000 ppm.
    • The Darco treatment is necessary to reduce the metal content in the product. Before treatment the levels are >20000 ppm.
  • 44
    • 79951626143 scopus 로고    scopus 로고
    • Isolation of the product and resubjecting the esters to the same epimerization conditions did not change the trans / cis ratio observed.
    • Isolation of the product and resubjecting the esters to the same epimerization conditions did not change the trans / cis ratio observed.
  • 45
    • 79951655996 scopus 로고    scopus 로고
    • The rate of dissolution or solubility of different NaOEt sources in ethanol may explain the different results observed.
    • The rate of dissolution or solubility of different NaOEt sources in ethanol may explain the different results observed.
  • 46
    • 79951624817 scopus 로고    scopus 로고
    • A full mechanism analysis is underway and will be reported in due course.
    • A full mechanism analysis is underway and will be reported in due course.
  • 47
    • 79951606662 scopus 로고    scopus 로고
    • Alternatively 10 equiv of TFA can be used with carefull monitoring of the KF.
    • Alternatively 10 equiv of TFA can be used with carefull monitoring of the KF.
  • 48
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    • Process for the preparation of diazabicyclo[3.3.1]nonane derivatives. WO 2008/088690 A2.
    • Gauvreau, D.; Huffman, M. A.; Hughes, G.; Itoh, T.; Yin, J.; Lau, S.; O'Shea, P. Process for the preparation of diazabicyclo[3.3.1]nonane derivatives. WO 2008/088690 A2, 2008.
    • (2008)
    • Gauvreau, D.1    Huffman, M.A.2    Hughes, G.3    Itoh, T.4    Yin, J.5    Lau, S.6    O'Shea, P.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.