Doranidazole, PR-000350, PR-350, RP-343

1,2,4-丁烯醇,3-[(2-硝基-1H-吡达唑-1-酰基)甲氧基]-, (2R,3S)-rel-Chemical Name: (?-1-[2,3-Dihydroxy-1-(hydroxymethyl)propoxymethyl]-2-nitroimidazole; (?-(2RS,3SR)-3-(2-Nitro-1H-imidazol-1-ylmethoxy)butane-1,2,4-triol
CAS No. 149838-23-3, 137339-64-1 (no stereoch)
项目整合开发状态: Phase I
项目研究机构: Pola Chemical (Originator)
合成路线:The acetylation of meso-erythritol (I) with 3 equivalents of Ac2O in pyridine gives 1,3,4-triacetoxy-meso-erythritol (II) with some tetraacetoxy derivative that is separated by chromatography.The reaction of (II) with P2O5 and dimethoxyethane yields 1,3,4-triacetoxy-2-(methoxymethoxy)butane (III),which is treated with Ac2O and BF3/Et2O to afford 1,3,4-triacetoxy-2-(acetoxymethoxy)butane (IV).The condensation of (IV) with 2-nitroimidazole (V) by means of Ts-OH at 130 C or by means of hot N,N-bis(trimethylsilyl)acetamide (BSA) provides the precursor (VI),which is finally deacetylated by means of EtONa in ethanol or TEA in aqueous methanol to furnish the target trihydroxy derivative.