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【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
      N-[1(R)-(3-Methoxyphenyl)-2(S)-phosphonoxypropyl]octanamide 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
Extended Information