An Efficient Large-Scale Process for the Human Leukocyte Elastase Inhibitor, DMP 7771

L Storace, L Anzalone, PN Confalone…

Index: Storace, Louis; Anzalone, Luigi; Confalone, Pat N.; Davis, Wayne P.; Fortunak, Joseph M.; Giangiordano, Mark; Haley Jr., James J.; Kamholz, Kenneth; Li, Hui-Yin; Ma, Philip; Nugent, William A.; Parsons Jr., Rodney L.; Sheeran, Patrick J.; Silverman, Charlotte E.; Waltermire, Robert E.; Wood, Christopher C. Organic Process Research and Development, 2002 , vol. 6, # 1 p. 54 - 63

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Citation Number: 30

Abstract

This report describes a new convergent, selective, and economical synthesis of DMP 777, 1 ending with the coupling of the chiral β-lactam half of the molecule (1) to the chiral amine as the isocyanate (2). Other steps involve the coupling of the β-lactam 3 to the phenolic moiety under phase-transfer conditions, followed by resolution of the resulting piperazine derivative using a chiral acid, and recycling of the undesired enantiomer also under phase-transfer ...