TY - JOUR
T1 - Crystallization-Induced Asymmetric Transformation
T2 - Stereospecific Synthesis of a Potent Peripheral CCK Antagonist
AU - Reider, Paul J.
AU - Davis, Paul
AU - Hughes, David L.
AU - Grabowski, Edward J.J.
PY - 1987/3/1
Y1 - 1987/3/1
N2 - An efficient, catalytic method for the total conversion of a racemate into a single enantiomer is reported. The combined, in situ resolution-racemization was applied to 3(RS)-amino-l,3-dihydro-l-methyl-5-phenyl-2tf-l,4-benzodiazepin-2-one to produce the optically pure S enantiomer in 91% yield. Acylation with indole-2-carboxylic acid produced L-364,718, an extremely potent nonpeptidal peripheral CCK antagonist.
AB - An efficient, catalytic method for the total conversion of a racemate into a single enantiomer is reported. The combined, in situ resolution-racemization was applied to 3(RS)-amino-l,3-dihydro-l-methyl-5-phenyl-2tf-l,4-benzodiazepin-2-one to produce the optically pure S enantiomer in 91% yield. Acylation with indole-2-carboxylic acid produced L-364,718, an extremely potent nonpeptidal peripheral CCK antagonist.
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U2 - 10.1021/jo00381a052
DO - 10.1021/jo00381a052
M3 - Letter
AN - SCOPUS:0023157368
SN - 0022-3263
VL - 52
SP - 955
EP - 957
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -