【结 构 式】 |
【分子编号】58332 【品名】(rac)-2-hydroxy-3-(1H-indol-3-yl)butanoic acid 【CA登记号】 |
【 分 子 式 】C12H13NO3 【 分 子 量 】219.24016 【元素组成】C 65.74% H 5.98% N 6.39% O 21.89% |
合成路线1
该中间体在本合成路线中的序号:(IV)The condensation of the chiral epoxide (I) with indole (II) by means of methylmagnesium bromide in ethyl ether/dichloromethane gives the indolylbutyric ester (III), which is hydrolyzed with NaOH in ethanol/water and purified by crystallization to yield the corresponding butyric acid (IV). The esterification of (IV) with ethanol/HCl regenerates pure ester (III), which is cyclized with guanidine (V) by means of tBu-OK in tert-butanol to afford the oxazolone (VI). Finally the amino group of (VI) is methylated by means of methylamine in water to provide the target indolmycin.
【1】 Hasuoka, A.; et al.; Development of a stereoselective practical synthetic route to indolmycin, a candidate anti-H. pylori agent. Chem Pharm Bull 2001, 49, 12, 1604. |
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) | 52089 | ethyl (2S,3R)-3-methyl-2-oxiranecarboxylate | C6H10O3 | 详情 | 详情 | |
(II) | 15292 | Indole; 1H-indole | 120-72-9 | C8H7N | 详情 | 详情 |
(III) | 52090 | ethyl (2S,3R)-2-hydroxy-3-(1H-indol-3-yl)butanoate | C14H17NO3 | 详情 | 详情 | |
(IV) | 58332 | (rac)-2-hydroxy-3-(1H-indol-3-yl)butanoic acid | C12H13NO3 | 详情 | 详情 | |
(V) | 14790 | Guanidine | 113-00-8 | CH5N3 | 详情 | 详情 |
(VI) | 52091 | (5S)-2-amino-5-[(1R)-1-(1H-indol-3-yl)ethyl]-1,3-oxazol-4(5H)-one | C13H13N3O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(III)The condensation of trans-epoxide (I) with indole (II) gives the racemic indolylbutyric acid (III), which is submitted to optical resolution with (+)-alpha-phenylethylamine to yield the (2S,3R)-enantiomer (2S,3R) (III). Finally, this compound is cyclized with N,N'.dimethylguanidine (IV) by means of Et-ONa in refluxing ethanol to afford the target indolmycin.
【1】 Preobrazhenskaya, M.N.; et al.; Total synthesis of antibiotic indolmycin and its stereoisomers. Tetrahedron 1968, 24, 6131. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(2S,3R)(III) | 58333 | (2S,3R)-2-hydroxy-3-(1H-indol-3-yl)butanoic acid | C12H13NO3 | 详情 | 详情 | |
(I) | 52089 | ethyl (2S,3R)-3-methyl-2-oxiranecarboxylate | C6H10O3 | 详情 | 详情 | |
(II) | 15292 | Indole; 1H-indole | 120-72-9 | C8H7N | 详情 | 详情 |
(III) | 58332 | (rac)-2-hydroxy-3-(1H-indol-3-yl)butanoic acid | C12H13NO3 | 详情 | 详情 | |
(IV) | 58334 | N,N'-dimethylguanidine | C3H9N3 | 详情 | 详情 |