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【结 构 式】

【分子编号】38082

【品名】methyl (E)-2-(acetamido)-3-dibenzo[b,d]furan-3-yl-2-propenoate

【CA登记号】

【 分 子 式 】C18H15NO4

【 分 子 量 】309.32144

【元素组成】C 69.89% H 4.89% N 4.53% O 20.69%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

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:(III)

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
Extended Information