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【结 构 式】 
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【分子编号】38085 【品名】methyl (2R)-2-(acetamido)-3-dibenzo[b,d]furan-3-ylpropanoate 【CA登记号】 |
【 分 子 式 】C18H17NO4 【 分 子 量 】311.33732 【元素组成】C 69.44% H 5.5% N 4.5% O 20.56% |
合成路线1
该中间体在本合成路线中的序号：(VI)The chiral amino acid (V) was prepared by two alternative procedures. Heck coupling between 3-iododibenzofuran (I) and methyl 2-acetamidoacrylate (II) in the presence of palladium diacetate afforded the alpha,beta-unsaturated alpha-amido ester (III), which was hydrogenated over Pd/C to yield the racemic saturated ester (IV). Incubation of (IV) with alcalase led to the enantiospecific hydrolysis of the S-enantiomer to give the required S-carboxylic acid (V). The unreacted R-enantiomer (VI) was recycled by epimerization in the presence of DBU.
| 【1】 Blanchard, L.; De Lombaert, S.; Stamford, L.B.; et al.; Potent and selective non-peptidic inhibitors of endothelin-converting enzyme-1 with sustained duration of action. J Med Chem 2000, 43, 3, 488. |
| 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) | 38080 | 3-iododibenzo[b,d]furan | C12H7IO | 详情 | 详情 | |
| (II) | 38081 | methyl 2-(acetamido)acrylate | 35356-70-8 | C6H9NO3 | 详情 | 详情 |
| (III) | 38082 | methyl (E)-2-(acetamido)-3-dibenzo[b,d]furan-3-yl-2-propenoate | C18H15NO4 | 详情 | 详情 | |
| (IV) | 38083 | methyl 2-(acetamido)-3-dibenzo[b,d]furan-3-ylpropanoate | C18H17NO4 | 详情 | 详情 | |
| (V) | 38084 | (2S)-2-(acetamido)-3-dibenzo[b,d]furan-3-ylpropionic acid | C17H15NO4 | 详情 | 详情 | |
| (VI) | 38085 | methyl (2R)-2-(acetamido)-3-dibenzo[b,d]furan-3-ylpropanoate | C18H17NO4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)The chiral amino acid (V) was prepared by two alternative procedures. Heck coupling between 3-iododibenzofuran (I) and methyl 2-acetamidoacrylate (II) in the presence of palladium diacetate afforded the alpha,beta-unsaturated alpha-amido ester (III), which was hydrogenated over Pd/C to yield the racemic saturated ester (IV). Incubation of (IV) with alcalase led to the enantiospecific hydrolysis of the S-enantiomer to give the required S-carboxylic acid (V). The unreacted R-enantiomer (VI) was recycled by epimerization in the presence of DBU.
| 【1】 Blanchard, L.; De Lombaert, S.; Stamford, L.B.; et al.; Potent and selective non-peptidic inhibitors of endothelin-converting enzyme-1 with sustained duration of action. J Med Chem 2000, 43, 3, 488. |
| 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) | 38080 | 3-iododibenzo[b,d]furan | C12H7IO | 详情 | 详情 | |
| (II) | 38081 | methyl 2-(acetamido)acrylate | 35356-70-8 | C6H9NO3 | 详情 | 详情 |
| (III) | 38082 | methyl (E)-2-(acetamido)-3-dibenzo[b,d]furan-3-yl-2-propenoate | C18H15NO4 | 详情 | 详情 | |
| (IV) | 38083 | methyl 2-(acetamido)-3-dibenzo[b,d]furan-3-ylpropanoate | C18H17NO4 | 详情 | 详情 | |
| (V) | 38084 | (2S)-2-(acetamido)-3-dibenzo[b,d]furan-3-ylpropionic acid | C17H15NO4 | 详情 | 详情 | |
| (VI) | 38085 | methyl (2R)-2-(acetamido)-3-dibenzo[b,d]furan-3-ylpropanoate | C18H17NO4 | 详情 | 详情 |