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【结 构 式】

【分子编号】49416

【品名】1-Chloro-3-iodopropane

【CA登记号】6940-76-7

【 分 子 式 】C3H6ClI

【 分 子 量 】204.43781

【元素组成】C 17.63% H 2.96% Cl 17.34% I 62.07%

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)

The condensation of N-(tert-butyldimethylsilyl)-4-oxoazetidine-2(S)-carboxylic acid (I) with 1-chloro-3-iodopropane (II) by means of BuLi and triisopropylamine (TIA) in THF, followed by treatment with HCl, gives the 3(R)-(3-chloropropyl) derivative (III), which is treated with tetrabutylammonium azide and tetrabutylammonium iodide in DMF to yield the 3-azidopropyl derivative (IV). The reduction of (IV) with H2 over Pd/C in DMF affords the 3-aminopropyl compound (V), which is treated with 1-[N,N'-bis(benzyloxycarbonyl)-1H-pyrazole] (VI) in the same solvent to provide the protected 3-guanidinopropyl compound (VII). The esterification of (VII) with NaHCO3, tetrabutylammonium iodide and Bn-Br in DMF gives the benzyl ester (VIII), which is condensed with N-tert-butylpiperazine-1-carboxamide (IX) and phosgene by means of TEA in toluene to yield the protected precursor (X). Finally, this compound is debenzylated by hydrogenation with H2 over Pd/C in dioxane to give the target azetidine-carboxylic acid.

1 Treuner, U.; Kronenthal, D.R.; Xu, Z.; Seiler, S.; Slusarchyk, W.A.; Bisacchi, G.; Randazzo, M.E.; Sutton, J.C.; Shi, Z.; Zahler, R.; Schwinden, M.D. (Bristol-Myers Squibb Co.); Amidino and guanidino azetidinone tryptase inhibitors. WO 9967215 .
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) 49426 (2S)-1-[tert-butyl(dimethyl)silyl]-4-oxo-2-azetidinecarboxylic acid C10H19NO3Si 详情 详情
(II) 49416 1-Chloro-3-iodopropane 6940-76-7 C3H6ClI 详情 详情
(III) 49417 (2S,3R)-3-(3-chloropropyl)-4-oxo-2-azetidinecarboxylic acid C7H10ClNO3 详情 详情
(IV) 49418 (2S,3R)-3-(3-azidopropyl)-4-oxo-2-azetidinecarboxylic acid C7H10N4O3 详情 详情
(V) 49419 (2S,3R)-3-(3-aminopropyl)-4-oxo-2-azetidinecarboxylic acid C7H12N2O3 详情 详情
(VI) 49420 benzyl (E)-[[(benzyloxy)carbonyl]amino](1H-pyrazol-1-yl)methylidenecarbamate C20H18N4O4 详情 详情
(VII) 49421 (2S,3R)-3-[3-[([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)amino]propyl]-4-oxo-2-azetidinecarboxylic acid C24H26N4O7 详情 详情
(VIII) 49422 benzyl (2S,3R)-3-[3-[([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)amino]propyl]-4-oxo-2-azetidinecarboxylate C31H32N4O7 详情 详情
(IX) 49423 N-(tert-butyl)-1-piperazinecarboxamide C9H19N3O 详情 详情
(X) 49424 benzyl (2S,3R)-3-[3-[([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)amino]propyl]-1-([4-[(tert-butylamino)carbonyl]-1-piperazinyl]carbonyl)-4-oxo-2-azetidinecarboxylate C41H49N7O9 详情 详情
(XI) 13225 N-tert-Butoxycarbonyl piperazine; tert-butyl 1-piperazinecarboxylate;tert-butyl piperazine-1-carboxylate 143238-38-4 C9H18N2O2 详情 详情
(XII) 16976 tert-butylisocyanate; tert-butyl isocyanate; 2-isocyanato-2-methylpropane 1609-86-5 C5H9NO 详情 详情
(XIII) 49425 tert-butyl 4-[(tert-butylamino)carbonyl]-1-piperazinecarboxylate C14H27N3O3 详情 详情
Extended Information