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【结 构 式】

【分子编号】33083

【品名】benzyl 3-chloro-7-([2-[4-chloro-2-(tritylamino)-1,3-thiazol-5-yl]-2-[(trityloxy)imino]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

【CA登记号】

【 分 子 式 】C57H43Cl2N5O5S2

【 分 子 量 】1013.03652

【元素组成】C 67.58% H 4.28% Cl 7% N 6.91% O 7.9% S 6.33%

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)

The condensation of 1,3-dichloroacetone (I) with thiourea (II) provided 2-amino-4-(chloromethyl)thiazole (III). Further displacement of the chlorine atom of (III) with N-Boc-2-mercaptoethylamine (IV) gave thioether (V). Thiocyanation of the thiazole ring of (V) using thiocyanogen, generated from KSCN and Br2, provided (VI). Reductive cleavage of the thiocyanate group of (VI) with NaBH4 gave rise to the mercaptothiazole (VII), which was subsequently coupled with the chlorocephem (VIII) to yield adduct (IX). Incorporation of a N-Boc-alanine unit to (IX) to afford (XI) was then achieved by condensation with N-Boc-alanine pentafluorophenyl ester (X) in 1,2-dichloroethane. Finally, the protecting groups of (XI) were cleaved by treatment with trifluoroacetic acid in the presence of triethylsilane.

1 Glinka, T.; Price, M.; Halas, S.; Calkins,T.; Frith, R.; Nudelman, G.; Whitehead, C.; Cho, A.; Hecker, S.; Ludwikow, M.; Chamberland, S.; Crawford, J.; Lee, V.; Design, synthesis and in vitro antibacterial properties of novel 3-heteroarylthio cephems with anti-MRSA activity: Amino acid prodrug approach to solubility improvement. 39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999, San Francisco) 1999, Abst F391.
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) 63907 1,3-dichloroacetone C3H4Cl2O 详情 详情
(II) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(III) 33078 4-(chloromethyl)-1,3-thiazol-2-amine; 4-(chloromethyl)-1,3-thiazol-2-ylamine C4H5ClN2S 详情 详情
(IV) 33079 tert-butyl 2-sulfanylethylcarbamate C7H15NO2S 详情 详情
(V) 33080 tert-butyl 2-[[(2-amino-1,3-thiazol-4-yl)methyl]sulfanyl]ethylcarbamate C11H19N3O2S2 详情 详情
(VI) 33081 tert-butyl 2-([[2-amino-5-(cyanosulfanyl)-1,3-thiazol-4-yl]methyl]sulfanyl)ethylcarbamate C12H18N4O2S3 详情 详情
(VII) 33082 tert-butyl 2-[[(2-amino-5-sulfanyl-1,3-thiazol-4-yl)methyl]sulfanyl]ethylcarbamate C11H19N3O2S3 详情 详情
(VIII) 33083 benzyl 3-chloro-7-([2-[4-chloro-2-(tritylamino)-1,3-thiazol-5-yl]-2-[(trityloxy)imino]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C57H43Cl2N5O5S2 详情 详情
(IX) 33084 benzyl 3-([2-amino-4-[([2-[(tert-butoxycarbonyl)amino]ethyl]sulfanyl)methyl]-1,3-thiazol-5-yl]sulfanyl)-7-([2-[4-chloro-2-(tritylamino)-1,3-thiazol-5-yl]-2-[(trityloxy)imino]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C68H61ClN8O7S5 详情 详情
(X) 33085 2,3,4,5,6-pentafluorophenyl (2S)-2-[(tert-butoxycarbonyl)amino]propanoate C14H14F5NO4 详情 详情
(XI) 33086 benzyl 3-[[4-[([2-[(tert-butoxycarbonyl)amino]ethyl]sulfanyl)methyl]-2-([(2S)-2-[(tert-butoxycarbonyl)amino]propanoyl]amino)-1,3-thiazol-5-yl]sulfanyl]-7-([2-[4-chloro-2-(tritylamino)-1,3-thiazol-5-yl]-2-[(trityloxy)imino]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; benzyl 3-[[4-[([2-[(tert-butoxycarbonyl)amino]ethyl]sulfanyl)methyl]-2-([(2S)-2-[(tert-butoxycarbonyl)amino]propanoyl]amino)-1,3-thiazol-5-yl]sulfanyl]-7-([2-[4-chloro-2-(tritylamino)-1,3-thiazol-5-yl]-2-[(trityloxy)imino]acetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C76H74ClN9O10S5 详情 详情
Extended Information