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【结 构 式】

【分子编号】48674

【品名】2-(2,2-diethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

【CA登记号】

【 分 子 式 】C16H24O5S

【 分 子 量 】328.42956

【元素组成】C 58.51% H 7.37% O 24.36% S 9.76%

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)

A new strategy for the synthesis of a key intermediate in the preparation of LY-333531 has been described: Condensation of indole (I) with the tosylate (II) by means of NaH in DMF gives 4-(1-indolyl)butane-1,2-diol (III), which is monotritylated with trityl bromide yielding ether (IV). Alkylation of compound (IV) with tert-butyl bromoacetate (V) and NaH in THF affords the hydroxyacetic derivative (VI), which is reduced with LiBH4 in THF/EtOH to provide the carbinol (VII). Reaction of compound (VII) with Ms2O and pyridine in THF gives the mesylate (VIII), which is condensed with oxalyl chloride (IX) in ethyl ether to yield the oxoacetyl chloride (X). The alcoholysis of (X) with NaOMe in methanol affords the oxoacetate (XI), which is finally cyclized with 2-(3-indolyl)acetamide (XII) by means of NaH in DMF to provide the target intermediate (XIII).

1 Faul, M.M.; Kumrich, C.A.; Cyclization strategies for the synthesis of macrocyclic bisindolylmaleimides. J Org Chem 2001, 66, 6, 2024.
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) 15292 Indole; 1H-indole 120-72-9 C8H7N 详情 详情
(II) 48674 2-(2,2-diethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate C16H24O5S 详情 详情
(III) 48675 4-(1H-indol-1-yl)-1,2-butanediol C12H15NO2 详情 详情
(IV) 48676 4-(1H-indol-1-yl)-1-(trityloxy)-2-butanol C31H29NO2 详情 详情
(V) 17430 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate 5292-43-3 C6H11BrO2 详情 详情
(VI) 48677 tert-butyl 2-[3-(1H-indol-1-yl)-1-[(trityloxy)methyl]propoxy]acetate C37H39NO4 详情 详情
(VII) 48678 2-[3-(1H-indol-1-yl)-1-[(trityloxy)methyl]propoxy]-1-ethanol C33H33NO3 详情 详情
(VIII) 48679 2-[3-(1H-indol-1-yl)-1-[(trityloxy)methyl]propoxy]ethyl methanesulfonate C34H35NO5S 详情 详情
(IX) 29841 Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride 79-37-8 C2Cl2O2 详情 详情
(X) 48680 2-[3-[3-(2-chloro-2-oxoacetyl)-1H-indol-1-yl]-1-[(trityloxy)methyl]propoxy]ethyl methanesulfonate C36H34ClNO7S 详情 详情
(XI) 48681 methyl 2-[1-[3-[2-[(methylsulfonyl)oxy]ethoxy]-4-(trityloxy)butyl]-1H-indol-3-yl]-2-oxoacetate C37H37NO8S 详情 详情
(XII) 48682 Indole-3-acetamide;3-Indoleacetamide;2-(1H-indol-3-yl) 879-37-8 C10H10N2O 详情 详情
(XIII) 48683 18-[(trityloxy)methyl]-17-oxa-4,14,21-triazahexacyclo[19.6.1.1(7,14).0(2,6).0(8,13).0(22,27)]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione C45H37N3O4 详情 详情
Extended Information