메뉴 건너뛰기




Volumn 12, Issue 2, 2008, Pages 218-225

Development of a pratical synthisis of DPP IV inhibitor LY2497282

Author keywords

[No Author keywords available]

Indexed keywords


EID: 58149142646     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op700235c     Document Type: Article
Times cited : (11)

References (50)
  • 1
    • 3843072211 scopus 로고    scopus 로고
    • (a) Weber, A. J. Med. Chem. 2004, 47, 4135.
    • (2004) J. Med. Chem , vol.4 , Issue.7 , pp. 4135
    • Weber, A.1
  • 11
    • 58149153546 scopus 로고    scopus 로고
    • Blaszczak, L. C.; Mathes, B. M.; Pulley, S. R.; Robertson, M. A.; Sheehan, S. M.: Shi. Q.; Watson, B. M.; Wiley, M. R. WO 2007/015767 Al, 2007.
    • Blaszczak, L. C.; Mathes, B. M.; Pulley, S. R.; Robertson, M. A.; Sheehan, S. M.: Shi. Q.; Watson, B. M.; Wiley, M. R. WO 2007/015767 Al, 2007.
  • 14
    • 58149147965 scopus 로고    scopus 로고
    • Eur. Pat. Appl. EP934923A1
    • (c) Satoh. H.; Turk, G. H. Eur. Pat. Appl. EP934923A1, 1999.
    • (1999)
    • Satoh, H.1    Turk, G.H.2
  • 19
    • 58149170864 scopus 로고    scopus 로고
    • Ketones 9a and 9b were observed as a mixture of ketone and enone forms in NMR.
    • Ketones 9a and 9b were observed as a mixture of ketone and enone forms in NMR.
  • 20
    • 0037064525 scopus 로고    scopus 로고
    • A similar predeprotonation protocol has been reported in the synthesis of α-(N-Boc-amino)ketones from α-(N-Boc-amino)Weinreb amide: Liu, J.; Ikemoto, N.; Petrillo, D.; Armstrong, J. D Tetrahedron Lett. 2002, 43, 8223.
    • A similar predeprotonation protocol has been reported in the synthesis of α-(N-Boc-amino)ketones from α-(N-Boc-amino)Weinreb amide: Liu, J.; Ikemoto, N.; Petrillo, D.; Armstrong, J. D Tetrahedron Lett. 2002, 43, 8223.
  • 21
    • 58149163965 scopus 로고    scopus 로고
    • The preparation of dianion-8 was described in the subsequent text in the Scheme 4 approach.
    • The preparation of dianion-8 was described in the subsequent text in the Scheme 4 approach.
  • 34
    • 85004804006 scopus 로고    scopus 로고
    • To fund the lab development of the subsequent steps, we also developed the synthesis of amino ester 14. The synthesis involved a classical Erlenmeyer condensation of 2,4-difluorobenzyaldehyde with N-acetyl glycine, followed by azlactone ring-opening to afford the corresponding dehydroamino ester. Amino ester 14 was further obtained from the dehydramino ester in >99% ee through enzyme resolution or asymmetric hydrogenation approach. For references on the synthesis of amino acids and derivatives, see: Roper, J. M.; Bauer, D. P. Synthesis 1983, 1041.
    • (a) To fund the lab development of the subsequent steps, we also developed the synthesis of amino ester 14. The synthesis involved a classical Erlenmeyer condensation of 2,4-difluorobenzyaldehyde with N-acetyl glycine, followed by azlactone ring-opening to afford the corresponding dehydroamino ester. Amino ester 14 was further obtained from the dehydramino ester in >99% ee through enzyme resolution or asymmetric hydrogenation approach. For references on the synthesis of amino acids and derivatives, see: Roper, J. M.; Bauer, D. P. Synthesis 1983, 1041.
  • 38
    • 33947732100 scopus 로고    scopus 로고
    • Cativiela, C; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2007, 18, 569.
    • (e) Cativiela, C; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2007, 18, 569.
  • 44
    • 58149162298 scopus 로고    scopus 로고
    • Lower yield was due to the recovery of aldehyde starting material 12, which may be caused by the aldehyde enolization during the dianion 8 addition. The hypothesis was that the extra diisopropylamine might help suppress the enolization of the aldehyde.
    • Lower yield was due to the recovery of aldehyde starting material 12, which may be caused by the aldehyde enolization during the dianion 8 addition. The hypothesis was that the extra diisopropylamine might help suppress the enolization of the aldehyde.
  • 49
    • 58149167338 scopus 로고    scopus 로고
    • The FTIR instrument is a Mettler-Toledo ReactIR-4000 equippe with a DiComp diamond sensor, a liquid nitrogen cooled MCT detector. Software version ReactIR 3.0 is used.
    • The FTIR instrument is a Mettler-Toledo ReactIR-4000 equippe with a DiComp diamond sensor, a liquid nitrogen cooled MCT detector. Software version ReactIR 3.0 is used.
  • 50
    • 0029019630 scopus 로고    scopus 로고
    • Ng, J. S.; Przybyla, C. A; Liu, C.; Yen, J. C.; Muellner, F. W.; Weyker, C. L. Tetrahedron 1995, 51, 6397.
    • Ng, J. S.; Przybyla, C. A; Liu, C.; Yen, J. C.; Muellner, F. W.; Weyker, C. L. Tetrahedron 1995, 51, 6397.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.