A short, scaleable synthesis of both enantiomers of 2-benzoylsulfanyl-5-phthalimidopentanoic acid from ornithine

An efficient “one-pot” synthesis of (R)- and (S)-2-bromo-5-phthalimidopentanoic acid from ornithine is described. Subsequent reaction with potassium thiobenzoate affords a concise, scaleable route to (R)- and (S)-enantiomers of 2-benzoylsulfanyl-5-phthalimidopentanoic acid, an intermediate in the sy...

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Bibliographic Details
Published in:Tetrahedron letters 1997-11, Vol.38 (47), p.8253-8256
Main Authors: Holt, Karen E., Hutton, Gordon E., Morfitt, C.Neil, Ruecroft, Graham, Taylor, Stephen J.C., Tiffin, Peter D., Tremayne, Neil, Woods, Martin
Format: Article
Language:English
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Summary:An efficient “one-pot” synthesis of (R)- and (S)-2-bromo-5-phthalimidopentanoic acid from ornithine is described. Subsequent reaction with potassium thiobenzoate affords a concise, scaleable route to (R)- and (S)-enantiomers of 2-benzoylsulfanyl-5-phthalimidopentanoic acid, an intermediate in the synthesis of MMP inhibitors. An efficient “one-pot” synthesis of (R)-and (S)-2-bromo-5-phthaloylaminovaleric acid from ornithine is described. Subsequent reaction with potassium thiobenzoate affords a concise, scaleable route to (R)-and (S)-2-benzoylsulfanyl-5-phthalimidopentanoic acid, an intermediate in the synthesis of MMP inhibitors.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)10160-5