【结 构 式】 ![]() |
【药物名称】 【化学名称】Phosphoric acid 2(R)-(3-methoxyphenyl)-1(S)-methyl-2-(octanamido)ethyl monoester disodium salt 【CA登记号】289051-01-0, 289052-54-6 (free acid) 【 分 子 式 】C18H28NNa2O6P 【 分 子 量 】431.38036 |
【开发单位】Ono (Originator) 【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, TNF-alpha Production Inhibitors |
合成路线1
The chiral amino alcohol (I) is acylated with octanoic acid (II), using EDC and HOBt, to afford amide (III). The lithium alkoxide of (III) is then phosphorylated by dibenzyl phosphorochloridate, yielding phosphate ester (IV). Benzyl groups cleavage in (IV) is effected by catalytic hydrogenation of (IV) over Pd/C to produce acid (V), which is finally converted to the title disodium salt by treatment with NaOH in EtOH.
【1】 Matsui, T.; Ohmawari, N. (Ono Pharmaceutical Co., Ltd.); Drugs containing phosphoric acid derivs. as the active ingredient. EP 1156054; US 6495533; WO 0050429 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 57795 | (1R,2S)-1-amino-1-(3-methoxyphenyl)-2-propanol | C10H15NO2 | 详情 | 详情 | |
(II) | 11091 | Octanoic acid | 124-07-2 | C8H16O2 | 详情 | 详情 |
(III) | 57796 | N-[(1R,2S)-2-hydroxy-1-(3-methoxyphenyl)propyl]octanamide | C18H29NO3 | 详情 | 详情 | |
(IV) | 57797 | dibenzyl (1S,2R)-2-(3-methoxyphenyl)-1-methyl-2-(octanoylamino)ethyl phosphate | C32H42NO6P | 详情 | 详情 | |
(V) | 57798 | (1S,2R)-2-(3-methoxyphenyl)-1-methyl-2-(octanoylamino)ethyl dihydrogen phosphate | C18H30NO6P | 详情 | 详情 |