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【结 构 式】 
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【分子编号】17957 【品名】4-(Acetamido)-2-methoxybenzoic acid ethoxycarbonyl anhydride 【CA登记号】 |
【 分 子 式 】C13H15NO6 【 分 子 量 】281.26524 【元素组成】C 55.51% H 5.38% N 4.98% O 34.13% |
合成路线1
该中间体在本合成路线中的序号：(II)4-Acetylamino-2-methoxybenzoic acid (I) was treated with ethyl chloroformate and triethylamine in cold THF, and the intermediate mixed anhydride (II) was then condensed with endo-9-benzyl-9-azabicyclo [3.3.1]nonan-3-amine (III) to yield amide (IV). Hydrogenolysis of the benzyl group in the presence of Pearlman's catalyst provided secondary amine (V), which was alkylated with ethyl 4-bromobutyrate (VI) to give (VII). Aromatic chlorination with sulfuryl chloride at position 5 afforded (VIII) and, then, selective acetamide hydrolysis with 20% HCl in refluxing ethanol gave the target compound.
| 【1】 Ito, Y.; Kato, H.; Yasuda, S.; Iwasaki, N.; Nishino, H.; Takeshita, M. (Hokuriku Seiyaku Co., Ltd.); Benzamide deriv.. EP 0640601; US 5395832; US 5500422; WO 9214705 . |
| 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) | 17956 | 4-(acetamido)-2-methoxybenzoic acid | 4093-29-2 | C10H11NO4 | 详情 | 详情 |
| (II) | 17957 | 4-(Acetamido)-2-methoxybenzoic acid ethoxycarbonyl anhydride | C13H15NO6 | 详情 | 详情 | |
| (III) | 17958 | (1S,2S,5R)-9-benzyl-9-azabicyclo[3.3.1]non-2-ylamine; (1S,2S,5R)-9-benzyl-9-azabicyclo[3.3.1]nonan-2-amine | C15H22N2 | 详情 | 详情 | |
| (IV) | 17959 | 4-(acetamido)-N-[(1S,2S,5R)-9-benzyl-9-azabicyclo[3.3.1]non-2-yl]-2-methoxybenzamide | C25H31N3O3 | 详情 | 详情 | |
| (V) | 17960 | 4-(acetamido)-N-[(1S,2S,5R)-9-azabicyclo[3.3.1]non-2-yl]-2-methoxybenzamide | C18H25N3O3 | 详情 | 详情 | |
| (VII) | 17962 | ethyl 4-((1S,2S,5R)-2-[[4-(acetamido)-2-methoxybenzoyl]amino]-9-azabicyclo[3.3.1]non-9-yl)butanoate | C24H35N3O5 | 详情 | 详情 | |
| (VIII) | 17963 | ethyl 4-((1S,2S,5R)-2-[[4-(acetamido)-5-chloro-2-methoxybenzoyl]amino]-9-azabicyclo[3.3.1]non-9-yl)butanoate | C24H34ClN3O5 | 详情 | 详情 |