The improved synthesis of OPC-29030, a platelet adhesion inhibitor via diastereoselective oxidation of chiral non-racemic sulfide.
An improved synthetic route of OPC-29030, the platelet adhesion inhibitor, was established via the diastereoselective oxidation of a chiral non-racemic sulfide (R)-5 to (S(S))-6 by the catalytic oxidation using VO(acac)(2) and cumene hydroperoxide (CHP) in the presence of MS4A. Under the current condition, the diastereoselectivity was not influenced by the presence of moisture, and moderate to high selectivity (72% de) was obtained at -30 degrees C. The obtained sulfoxide, which diastereomeric excess was easily raised by the recrystallization, could successfully lead to OPC-29030.
Matsugi
Masato
M
Department of Materials Chemistry, Graduate School of Engineering, Osaka University, Japan. matsugi@ap.chem.eng.osaka-u.ac.jp
Shimada
Rieko
R
Ohata
Shinji
S
Nojima
Masatomo
M
Fukuda
Norio
N
Minamikawa
Jun-ichi
J
Kita
Yasuyuki
Y
D007093:Imidazoles; D010084:Oxidation-Reduction; D010973:Platelet Adhesiveness / Q000187:drug effects*; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D015363:Quinolones; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds
D007093:Imidazoles; C404198:OPC 29030; D010975:Platelet Aggregation Inhibitors; D015363:Quinolones; D013440:Sulfides; D013457:Sulfur Compounds