Synthesis of optically active NC-1800, a therapeutic agent for urinary disturbance.
A new synthetic method for chiral oxazolidinone derivatives, therapeutic agents for treating urinary disturbance, is described. The condensed compound obtained from chiral 1-amino-3-phenyl-2-propanol and 1-phenyl-3-morpholino-1-propanone was reduced with Me4NBH(OAc)3 to give the intermediate, 1-(3-morpholino-1-phenylpropyl)amino-3-phenyl-2-propanol (MAPP) in 34% diastereomeric excess (d.e.). MAPP was converted to an urethane and purified by recrystallization of its methanesulfonate, to afford a single isomer, (2R)-1-[N-[(1S)-3-morpholino-1-phenylpropyl]-N -ethoxycarbonyl]amino-3-phenyl-2-propanol methanesulfonate (4-A. methanesulfonate).
Yoshida
S
S
Department of Applied Chemistry, Faculty of Engineering, Saitama University, Japan.
Yamamoto
M
M
Mochizuki
N
N
Nohira
H
H
D007202:Indicators and Reagents; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D009125:Muscle Relaxants, Central / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D023303:Oxazolidinones; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014570:Urologic Diseases / Q000188:drug therapy*
D007202:Indicators and Reagents; D009025:Morpholines; D009125:Muscle Relaxants, Central; C108590:NC 1800; D010080:Oxazoles; D023303:Oxazolidinones