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【结 构 式】

【分子编号】16725

【品名】trimethylsulfonium iodide

【CA登记号】2181-42-2

【 分 子 式 】C3H9IS

【 分 子 量 】204.07493

【元素组成】C 17.66% H 4.45% I 62.19% S 15.71%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

1) The reaction of tert-butoxycarbonyl-L-prolinal (I) with trimethylsulfonium iodide (II) and potassium tert-butoxide gives the epoxide (III), which is treated with benzyl alcohol and NaH to perform epoxide ring opening and simultaneous cyclization to yield the oxazolidinone (IV). The hydrolysis of (IV) with KOH affords compound (V), which is condensed with N-(benzylaminocarbonyl)-L-proline (VI) (prepared in situ with benzyl isocyanate (VII) and L-proline (VIII) in the presence of triethylamine) by means of diphenyl phosphoryl azide (DPPA) giving the dipeptide analogue (IX). The oxidation of (IX) with P2O5 in DMSO yields the benzylated JTP-4819 product (X), which is finally deprotected by hydrogenolysis with H2 over Pd/C.

1 Wroblewski, T.; Silvestre, J.S.; Castañer, J.; JTP-4819. Drugs Fut 1998, 23, 4, 384.
2 Fujiwara, T.; Iwamoto, Y.; Uchida, I.; Shinoda, M.; Abe, H.; Toide, K.; A novel prolyl endopeptidase inhibitor, JTP-4819, for the treatment of Alzheimer's disease: Review of preclinical pharmacology. CNS Drug Rev 1996, 2, 3, 343-62.
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) 16724 tert-Butyl (2S)-2-formyltetrahydro-1H-pyrrole-1-carboxylate; tert-Butoxycarbonyl-L-prolinal 69610-41-9 C10H17NO3 详情 详情
(II) 16725 trimethylsulfonium iodide 2181-42-2 C3H9IS 详情 详情
(III) 16726 tert-butyl (2S)-2-[(2R)oxiranyl]tetrahydro-1H-pyrrole-1-carboxylate C11H19NO3 详情 详情
(IV) 16727 (1R,7aS)-1-[(benzyloxy)methyl]tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one C14H17NO3 详情 详情
(V) 16728 (1R)-2-(benzyloxy)-1-[(2S)tetrahydro-1H-pyrrol-2-yl]-1-ethanol C13H19NO2 详情 详情
(VI) 16729 (2S)-1-[(benzylamino)carbonyl]tetrahydro-1H-pyrrole-2-carboxylic acid C13H16N2O3 详情 详情
(VII) 16730 1-(Isocyanatomethyl)benzene; Benzyl Isocyanate 3173-56-6 C8H7NO 详情 详情
(VIII) 16731 L-proline 147-85-3 C5H9NO2 详情 详情
(IX) 16732 (2S)-N-benzyl-2-([(2S)-2-[(1R)-2-(benzyloxy)-1-hydroxyethyl]tetrahydro-1H-pyrrol-1-yl]carbonyl)tetrahydro-1H-pyrrole-1-carboxamide C26H33N3O4 详情 详情
(X) 16733 (2S)-N-benzyl-2-([(2S)-2-[2-(benzyloxy)acetyl]tetrahydro-1H-pyrrol-1-yl]carbonyl)tetrahydro-1H-pyrrole-1-carboxamide C26H31N3O4 详情 详情
Extended Information