【结 构 式】 |
【分子编号】52087 【品名】Ethyl crotonate; trans-Ethyl crotonate; Crotonic acid ethyl ester 【CA登记号】623-70-1 |
【 分 子 式 】C6H10O2 【 分 子 量 】114.1442 【元素组成】C 63.14% H 8.83% O 28.03% |
合成路线1
该中间体在本合成路线中的序号:(I)The title compound was isolated from the fermentation broth of Streptomyces sp. strain HC-21. A synthetic method for the preparation of the title compound was also reported. Asymmetric dihydroxylation of ethyl crotonate (I) using commercial AD-mix-beta produced diol (II). This was converted to the (2S,3R)-epoxide (III) by bromination with HBr in HOAc followed by cyclization of the resultant bromohydrin in the presence of DBU. Epoxide ring opening with the organomagnesium reagent generated from indole (IV) and methylmagnesium bromide furnished the chiral indolylbutanoate (V). Cyclization of the hydroxy ester (V) with guanidine hydrochloride (VI) in the presence of potassium tert-butoxide yielded the amino oxazolone (VII). Finally, displacement of the amino- by a methylamino group was achieved by treatment with aqueous methylamine.
【1】 Kanamaru, T.; Nakao, M.; Tawada, H.; Kamiyama, K. (Takeda Chemical Industries, Ltd.); Oxazolone derivs. and their use as anti-Helicobacter pylori agent. EP 0923577; JP 1998279579; US 6169102; WO 9749703 . |
【2】 Kamiyama, K.; Nakayama, Y. (Takeda Chemical Industries, Ltd.); Process for producing indolmycins. WO 9952905 . |
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) | 52087 | Ethyl crotonate; trans-Ethyl crotonate; Crotonic acid ethyl ester | 623-70-1 | C6H10O2 | 详情 | 详情 |
(II) | 52088 | ethyl (2S,3R)-2,3-dihydroxybutanoate | C6H12O4 | 详情 | 详情 | |
(III) | 52089 | ethyl (2S,3R)-3-methyl-2-oxiranecarboxylate | C6H10O3 | 详情 | 详情 | |
(IV) | 15292 | Indole; 1H-indole | 120-72-9 | C8H7N | 详情 | 详情 |
(V) | 52090 | ethyl (2S,3R)-2-hydroxy-3-(1H-indol-3-yl)butanoate | C14H17NO3 | 详情 | 详情 | |
(VI) | 14790 | Guanidine | 113-00-8 | CH5N3 | 详情 | 详情 |
(VII) | 52091 | (5S)-2-amino-5-[(1R)-1-(1H-indol-3-yl)ethyl]-1,3-oxazol-4(5H)-one | C13H13N3O2 | 详情 | 详情 |