【结 构 式】 |
【药物名称】 【化学名称】2-Oxo-N-[1(R)-Phenylethyl]-4-(2-pyridinylmethylsulfanyl)azetidine-1-carboxamide 【CA登记号】210492-77-6 【 分 子 式 】C18H19N3O2S 【 分 子 量 】341.43503 |
【开发单位】Boehringer Ingelheim (Originator) 【药理作用】Anti-Cytomegalovirus Drugs, ANTIINFECTIVE THERAPY, Antiviral Drugs, Protease Inhibitors |
合成路线1
The acylation of 2-pyridylmethanol (I) with thioacetic acid (II) by means of Ph3P and DEAD in THF gives the corresponding thioacetate (III), which is condensed with 4-acetoxyazetidin-2-one (IV) by means of NaOH in methanol yielding 4-(2-pyridylmethylsulfanyl)azetidin-2-one (V). Finally, this compound is condensed with 1(R)-phenylethyl isocyanate (VI) by means of Et3N and DMAP in dichloromethane.
【1】 Deziel, R.; Malenfant, E.; Inhibition of human cytomegalovirus protease N(o) with monocyclic beta-lactams. Bioorg Med Chem Lett 1998, 8, 11, 1437. |
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) | 30208 | 2-pyridinylmethanol;pyridin-2-ylmethanol;2-pyridylmethanol | 586-98-1 | C6H7NO | 详情 | 详情 |
(II) | 12893 | Ethanethioic S-acid | C2H4OS | 详情 | 详情 | |
(III) | 30209 | S-(2-pyridinylmethyl) ethanethioate | C8H9NOS | 详情 | 详情 | |
(IV) | 30210 | 4-oxo-2-azetidinyl acetate | C5H7NO3 | 详情 | 详情 | |
(V) | 30211 | 4-[(2-pyridinylmethyl)sulfanyl]-2-azetidinone | C9H10N2OS | 详情 | 详情 | |
(VI) | 30212 | 1-[(1R)-1-isocyanatoethyl]benzene; (1R)-1-phenylethyl isocyanate | 33375-06-3 | C9H9NO | 详情 | 详情 |
Extended Information