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【结 构 式】

【分子编号】42114

【品名】tert-butyl (2R)-4-(3-chlorophenyl)-2-[(ethylsulfonyl)methyl]-5-oxo-1-piperazinecarboxylate

【CA登记号】

【 分 子 式 】C18H25ClN2O5S

【 分 子 量 】416.92568

【元素组成】C 51.86% H 6.04% Cl 8.5% N 6.72% O 19.19% S 7.69%

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 reductive alkylation of 3-chloroaniline (I) with L-S-trityl-N-Boc-cysteinal (II) in the presence of sodium triacetoxyborohydride produced amine (III). Chloroacetylation of (III) followed by cesium carbonate-induced cyclization of the resulting chloroacetamide (IV) furnished the protected piperazinone (V). The S-trityl group of (V) was deprotected by treatment with silver nitrate and pyridine, yielding thiol (VI), which was subsequently alkylated with ethyl iodide to give thioether (VII). Sulfur oxidation by means of magnesium monoperoxyphthalate in methanol afforded sulfone (VIII). Then, acid deprotection of the Boc protecting group of (VIII) provided the intermediate piperazinone (IX).

1 Anthony, N.J.; Ciccarone, T.M.; Gomez, R.P.; Hutchinson, J.H.; Williams, T.M.; Dinsmore, C.J.; Stokker, G.E. (Merck & Co., Inc.); Inhibitors of farnesyl-protein transferase. EP 0820445; JP 1998511098; US 5856326; WO 9630343 .
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) 25239 3-chloroaniline; 3-chlorophenylamine 108-42-9 C6H6ClN 详情 详情
(II) 17953 tert-butyl (1R)-1-formyl-2-(tritylsulfanyl)ethylcarbamate C27H29NO3S 详情 详情
(III) 42109 tert-butyl (1R)-2-(3-chloroanilino)-1-[(tritylsulfanyl)methyl]ethylcarbamate C33H35ClN2O2S 详情 详情
(IV) 42110 tert-butyl (1R)-2-[3-chloro(2-chloroacetyl)anilino]-1-[(tritylsulfanyl)methyl]ethylcarbamate C35H36Cl2N2O3S 详情 详情
(V) 42111 tert-butyl (2R)-4-(3-chlorophenyl)-5-oxo-2-[(tritylsulfanyl)methyl]-1-piperazinecarboxylate C35H35ClN2O3S 详情 详情
(VI) 42112 tert-butyl (2R)-4-(3-chlorophenyl)-5-oxo-2-(sulfanylmethyl)-1-piperazinecarboxylate C16H21ClN2O3S 详情 详情
(VII) 42113 tert-butyl (2R)-4-(3-chlorophenyl)-2-[(ethylsulfanyl)methyl]-5-oxo-1-piperazinecarboxylate C18H25ClN2O3S 详情 详情
(VIII) 42114 tert-butyl (2R)-4-(3-chlorophenyl)-2-[(ethylsulfonyl)methyl]-5-oxo-1-piperazinecarboxylate C18H25ClN2O5S 详情 详情
(IX) 42115 (5R)-1-(3-chlorophenyl)-5-[(ethylsulfonyl)methyl]-2-piperazinone C13H17ClN2O3S 详情 详情
Extended Information