Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1998-08-14
2000-05-16
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
C07D22310
Patent
active
060639199
ABSTRACT:
A process for the synthesis of an Exochelin comprising the steps of generating L-N-[(2-benzyloxy-(benzoyl)] serine or L-N-[2-benzyloxy (benzoyl)] threonine, creating L-N-t-Boc-.epsilon.-hydroxynorleucine and reacting same to produce L-N-Boc-.epsilon.-bromonorleucine trimethylsilylethyl ester, providing a dicarboxylic acid and forming an O-benzyl methyl hydroxamate from the dicarboxylic acid, coupling the O-benzyl methyl hydroxamate with the L-N-Boc-.epsilon.-bromonorleucine trimethylsilylethyl ester to give an L-N.sup.2 -Boc-N.sup.6 -methyl,N.sup.6 -(benzyloxy) lysine 2-trimethylsilylethyl ester which incorporates the dicarboxylic acid as modified above, removing the N-tert-butoxycarbonyl protecting group from the L-N.sup.2 -Boc-N.sup.6 -methyl, N.sup.6 -(benzyloxy) lysine 2-trimethylsilylethyl ester to yield a substituted lysine, and coupling the same with the L-N-[2-benzyloxy (benzoyl) serine or -threonine to yield a 2-trimethyl silylethyl ester of dibenzyl Exochelic acid, transforming the 2-trimethyl silylethyl ester of dibenzyl Exochelic acid to dibenzyl Exochelic acid, preparing benzyl epi-cobactin, forming an ester bond between the dibenzyl Exochelic acid and benzyl epi-cobactin to form an intermediate, and, hydrogenolytically removing three benzyl groups from said intermediate, resulting in the synthesized Exochelin. More particularly, a synthesis for Exochelin 786SM (R) is disclosed wherein the dicarboxylic acid is suberic acid and the serine form is utilized.
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Gaudioso Larry A.
Weglarz Michael A.
Coleman Brenda
Keystone BioMedical, Inc.
Ram Michael J.
Shah Mukund J.
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