NC-1800

Chemical Name: (5RS,1'SR)-5-Benzyl-3-[3-(4-morpholinyl)-1-phenylpropyl]oxazolidin-2-one monofumarate
CAS No. 173273-43-3, 161214-65-9 (free base), 161214-64-8 (racemic, (R*,R*)-isomer, free base), 161214-66-0 (undefined isomer), 161214-50-2 (undefined isomer, free base)
项目整合开发状态: Phase II
项目研究机构: Nippon Chemiphar (Originator)
合成路线:The condensation of (R)-1-amino-3-phenyl-2-propanol (I) with 1-phenyl-3-(4-morpholinyl)-1-propanone (II) in benzene with azeotropic removal of water furnished the intermediate imine (III),which was reduced employing tetramethylammonium triacetoxyborohydride to produce aminoalcohol (IV) as a 2:1 diastereomeric mixture.Treatment of this mixture with ethyl chloroformate gave a mixture of carbamates,from which the required (1S,2R)-diastereoisomer (V) was isolated by recrystallization as the methanesulfonate salt.Cyclization of (V) with K2CO3 then yielded oxazolidinone (VI).This was finally treated with fumaric acid to provide the title fumarate salt.