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【结 构 式】

【分子编号】58935

【品名】ethyl (2Z)-2-(acetylamino)-2,8-nonadienoate

【CA登记号】

【 分 子 式 】C13H21NO3

【 分 子 量 】239.31468

【元素组成】C 65.25% H 8.84% N 5.85% O 20.06%

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:(V)

The aminoacid building block (VIII) can be prepared by two different ways. The oxidative cleavage of 7-octene-1,2-diol (I) by means of NaIO4 yields aldehyde (II). Partial hydrolysis of diethyl 2-acetamidomalonate (III) provides monoacid (IV), which is subjected to Knoevenagel-type condensation with 6-heptenal (II) in the presence of Ac2O and pyridine to afford enamide (V). Enantioselective hydrogenation of the enamide double bond to the (S)-amidoester (VI) is then achieved by using the Burk's method. In order to replace the N-acetyl protecting group of (VI), the acetamide nitrogen is protected with Boc2O, and the resulting imide (VII) is further hydrolyzed to the target N-Boc aminoacid (VIII) under standard basic conditions.

1 Halmos, T.; Llinas-Brunet, M.; Faucher, A.-M.; Ghiro, E.; Goudreau, N.; Tsantrizos, Y.S.; Cameron, D.R. (Boehringer Ingelheim (Canada) Ltd.); Macrocyclic peptides active against the hepatitis C virus. EP 1169339; JP 2002542160; WO 0059929 .
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) 58933 7-Octene-1,2-diol C8H16O2 详情 详情
(II) 27179 6-heptenal C7H12O 详情 详情
(III) 16170 1,2-dichloroethane 107-06-2 C2H4Cl2 详情 详情
(IV) 58934 Ethyl 2-acetamidomalonate C7H11NO5 详情 详情
(V) 58935 ethyl (2Z)-2-(acetylamino)-2,8-nonadienoate C13H21NO3 详情 详情
(VI) 58936 ethyl (2S)-2-(acetylamino)-8-nonenoate C13H23NO3 详情 详情
(VII) 58937 (2S)-2-[acetyl(tert-butoxycarbonyl)amino]-8-nonenoic acid C16H27NO5 详情 详情
(VIII) 58938 (2S)-2-[(tert-butoxycarbonyl)amino]-8-nonenoic acid C14H25NO4 详情 详情
Extended Information