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Volumn 40, Issue 11, 1999, Pages 2187-2190

Stereoselective synthesis of a candoxatril intermediate via asymmetric hydrogenation

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID BUTYL ESTER; ALKENE DERIVATIVE; CANDOXATRIL; MEMBRANE METALLOENDOPEPTIDASE; METALLOPROTEINASE INHIBITOR; PARA CYMENE; PROPIONIC ACID DERIVATIVE; PSEUDOEPHEDRINE; RUTHENIUM;

EID: 0033548571     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02687-2     Document Type: Article
Times cited : (16)

References (20)
  • 5
    • 0013581534 scopus 로고    scopus 로고
    • The four possible geometrical isomers of 8 and 9 were considered as possible asymmetric hydrogenation substrates. The enol ether isomers 9 failed to hydrogenate with the catalysts and conditions studied. Attempts to synthesise the Z isomer of 9 have so far been unsuccessful
    • The four possible geometrical isomers of 8 and 9 were considered as possible asymmetric hydrogenation substrates. The enol ether isomers 9 failed to hydrogenate with the catalysts and conditions studied. Attempts to synthesise the Z isomer of 9 have so far been unsuccessful.
  • 9
    • 0013629346 scopus 로고    scopus 로고
    • We thank Dr Jon Bordner of Pfizer Central Research, Groton for X-ray crystallographic studies. The data has been deposited at the Cambridge Crystallographic Data Center
    • We thank Dr Jon Bordner of Pfizer Central Research, Groton for X-ray crystallographic studies. The data has been deposited at the Cambridge Crystallographic Data Center.
  • 10
    • 4744362831 scopus 로고
    • For general reviews of the Baylis-Hillman reaction see: a) Drewes, S.E., Roos, G.H.P., Tetrahedron., 1988, 44, 4653-4670;
    • (1988) Tetrahedron , vol.44 , pp. 4653-4670
    • Drewes, S.E.1    Roos, G.H.P.2
  • 15
    • 0013582660 scopus 로고    scopus 로고
    • Pfizer Central Research, private communication
    • Wythes, M.J., Corless, G.P., Pfizer Central Research, private communication.
    • Wythes, M.J.1    Corless, G.P.2
  • 16
    • 0013614379 scopus 로고    scopus 로고
    • A long-range inverse-detected C-H correlation experiment showed a coupling constant of 7.0Hz between the olefinic proton and the t-butyl ester carbon and a 9Hz coupling between the olefinic proton and the methylene carbon of the MEM-side chain. This data is consistent with the (E)-stereochemistry
    • A long-range inverse-detected C-H correlation experiment showed a coupling constant of 7.0Hz between the olefinic proton and the t-butyl ester carbon and a 9Hz coupling between the olefinic proton and the methylene carbon of the MEM-side chain. This data is consistent with the (E)-stereochemistry.
  • 17
    • 0013605756 scopus 로고    scopus 로고
    • European Patent 0644176
    • Challenger, S., European Patent 0644176, Chem. Abs., 1996, 124, 55417.
    • (1996) Chem. Abs. , vol.124 , pp. 55417
    • Challenger, S.1
  • 18
    • 0013603239 scopus 로고    scopus 로고
    • Chiral HPLC assays for 4 were performed using a Daicel Chiralpak AD (250 × 4.6mm) column eluting with 95% n-hexane, 5% 2-propanol and 0.1% TFA. Flow rate 1.0 mL/min, detection UV-220 nm. Typical retention times were (S)-enantiomer 9.37 min, (R)-enantiomer 10.62 min
    • Chiral HPLC assays for 4 were performed using a Daicel Chiralpak AD (250 × 4.6mm) column eluting with 95% n-hexane, 5% 2-propanol and 0.1% TFA. Flow rate 1.0 mL/min, detection UV-220 nm. Typical retention times were (S)-enantiomer 9.37 min, (R)-enantiomer 10.62 min.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.