An efficient large-scale process for the human leukocyte elastase inhibitor, DMP 777
This report describes a new convergent, selective, and economical synthesis of DMP 777, 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 conditions. The chiral amine 4 was produced efficiently starting from (R)-α-methylbenzylamine and the corresponding butyrophenone.
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.
p. 54 - 63
(2013/09/06)
Asymmetric synthesis of R-α-propyl-piperonyl amine and its analogs
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(2008/06/13)
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