Preparation of α-keto ester enol acetates as potential prodrugs of human neutrophil elastase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 1, 1998, Pages 63-64

  Burkhart, Joseph P ^a   Mehdi, Shujaath ^a   Koehl, Jack R ^a   Angelastro, Michael R ^a   Bey, Philippe ^a   Peet, Norton P ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALPHA KETO ESTER ENOL ACETATE; ENZYME INHIBITOR; ESTER; LEUKOCYTE ELASTASE; PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; NONHUMAN;

ACETATES; ESTERS; HUMANS; LEUKOCYTE ELASTASE; PRODRUGS; PROTEASE INHIBITORS;

EID: 0032488581     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10184-6     Document Type: Article

References (13)

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12. +) calcd 555.2666; found 555.2665. Compound 4 was prepared using the same procedure in 16% yield. Spectral data were consistent with structure and confirmed the presence, in the purified sample, of only the E-isomer.
13. 10. A recent article describes a modified Dakin-West Procedure for related enol esters of α-keto esters. See Li, Z.; Ortega-Vilain, A.; Patel, G.S.; Chu, D.; Foreman, J. E.; Eveleth, D. D.; Powers, J.C. J. Med. Chem. 1996, 39, 4089.