【结 构 式】 |
【分子编号】30459 【品名】2-[[(2S)-2-(dibenzylamino)-3-phenylpropyl]oxy]-1-ethanol 【CA登记号】 |
【 分 子 式 】C25H29NO2 【 分 子 量 】375.5108 【元素组成】C 79.96% H 7.78% N 3.73% O 8.52% |
合成路线1
该中间体在本合成路线中的序号:(XII)The intermediate 2-(2(S)-amino-3-phenylpropoxy)ethanol (VII) has been obtained as follows: The condensation of 2(S)-(dibenzylamino)-3-phenyl-1-propanol (IX) with tert-butyl 2-bromoacetate (X) by means of tetrabutylammonium hydrogen sulfate and NaOH in dichloromethane/water gives 2-[2(S)-(dibenzylamino)-3-phenylpropoxy]acetic acid tert-butyl ester (XI), which is reduced with LiAlH4 in THF yielding 2-[2(S)-(dibenzylamino)-3-phenylpropoxy]ethanol (XII). Finally, this compound is debenzylated by hydrogenation with H2 over Pd/C in methanol/acetic acid affording the target intermediate (VII).
【1】 Brundish, D.E.; Brown, L.N.; Le Grand, D.M.; Menear, K.A.; Smith, G.P.; Allen, M.C.; Butler, P.I.; Cockroft, X.-L.; Matthews, I.T.W.; Walker, C.V.; Wathey, W.B. (Novartis AG); Thrombin inhibitors. WO 9746553 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VII) | 30455 | 2-[[(2S)-2-amino-3-phenylpropyl]oxy]-1-ethanol | C11H17NO2 | 详情 | 详情 | |
(IX) | 30457 | (2S)-2-(dibenzylamino)-3-phenyl-1-propanol | 111060-52-7 | C23H25NO | 详情 | 详情 |
(X) | 17430 | 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate | 5292-43-3 | C6H11BrO2 | 详情 | 详情 |
(XI) | 30458 | tert-butyl 2-[[(2S)-2-(dibenzylamino)-3-phenylpropyl]oxy]acetate | C29H35NO3 | 详情 | 详情 | |
(XII) | 30459 | 2-[[(2S)-2-(dibenzylamino)-3-phenylpropyl]oxy]-1-ethanol | C25H29NO2 | 详情 | 详情 |