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【结 构 式】

【分子编号】28438

【品名】(2S,3S)-3-amino-4-phenyl-1-[1-[4-(1,3-thiazol-2-yl)benzyl]hydrazino]-2-butanol

【CA登记号】

【 分 子 式 】C20H24N4OS

【 分 子 量 】368.50292

【元素组成】C 65.19% H 6.56% N 15.2% O 4.34% S 8.7%

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:(VIII)

4-Bromobenzaldehyde dimethyl acetal (I) was converted to the corresponding Grignard reagent and then coupled with 2-bromothiazole (II) in the presence of [1,3-bis(diphenylphosphino)propane]nickel chloride to afford 4-(2-thiazolyl)benzaldehyde dimethylacetal (III). After acid hydrolysis of the acetal group of (II), the resulting aldehyde was condensed with tert-butyl carbazate to give hydrazone (IV), which was further reduced to the benzylhydrazine (V) employing NaBH3CN and p-toluenesulfonic acid. Opening of the Boc-protected epoxide (VI) with hydrazine (V) gave hydrazinoalcohol (VII). Both Boc groups of (VII) were removed by treatment with formic acid to yield diamino compound (VIII). Finally, coupling of (VIII) with N-methoxycarbonyl-L-tert-leucine (IX) by means of O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetra fluoroborate (TPTU) provided the title bisamide.

1 New aza-dipeptide analogues as potent and orally a. J Med Chem 1998, 41, 18, 3387.
2 Fassler, A.; Bold, G.; Capraro, H.-G.; Lang, M.; Khanna, S.C. (Novartis AG); Antivirally active heterocyclic azahexane derivs.. EP 0900210; JP 1999511177; US 5849911; WO 9740029 .
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) 23438 (4-bromophenyl)(methoxy)methyl methyl ether; 1-bromo-4-(dimethoxymethyl)benzene C9H11BrO2 详情 详情
(II) 23161 2-bromo-1,3-thiazole 3034-53-5 C3H2BrNS 详情 详情
(III) 28434 2-[4-(dimethoxymethyl)phenyl]-1,3-thiazole C12H13NO2S 详情 详情
(IV) 28435 tert-butyl 2-[(Z)-[4-(1,3-thiazol-2-yl)phenyl]methylidene]-1-hydrazinecarboxylate C15H17N3O2S 详情 详情
(V) 28436 tert-butyl 2-[4-(1,3-thiazol-2-yl)benzyl]-1-hydrazinecarboxylate C15H19N3O2S 详情 详情
(VI) 23444 tert-butyl (1S)-1-[(2R)oxiranyl]-2-phenylethylcarbamate C15H21NO3 详情 详情
(VII) 28437 tert-butyl 2-[(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl]-2-[4-(1,3-thiazol-2-yl)benzyl]-1-hydrazinecarboxylate C30H40N4O5S 详情 详情
(VIII) 28438 (2S,3S)-3-amino-4-phenyl-1-[1-[4-(1,3-thiazol-2-yl)benzyl]hydrazino]-2-butanol C20H24N4OS 详情 详情
(IX) 23447 (2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutyric acid C8H15NO4 详情 详情
Extended Information