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【结 构 式】 
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【分子编号】61958 【品名】methyl (2S)-3-[3,4-bis(acetyloxy)phenyl]-2-[({5-[(E)-2-cyano-3-(diethylamino)-3-oxo-1-propenyl]-2-hydroxy-3-nitrophenoxy}carbonyl)amino]propanoate 【CA登记号】 |
【 分 子 式 】C29H30N4O12 【 分 子 量 】626.57696 【元素组成】C 55.59% H 4.83% N 8.94% O 30.64% |
合成路线1
该中间体在本合成路线中的序号：(VI)Esterification of L-Dopa (I) with thionyl chloride in methanol leads to the methyl ester (II). The phenolic hydroxyls of (II) are further acylated by acetyl chloride in trifluoroacetic acid to produce diacetate (III). Treatment of the protected derivative of L-Dopa (III) with diphosgene gives rise to isocyanate (IV). This is then coupled to entacapone (V) in refluxing acetonitrile to furnish carbamate (VI). The acetate ester groups of (VI) are finally removed by treatment with 3N HCl in acetone.
| 【1】 Leppanen, J.; et al.; Design and synthesis of a novel L-dopa-entacapone codrug. J Med Chem 2002, 45, 6, 1379. |
| 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) | 15272 | (2S)-2-amino-3-(3,4-dihydroxyphenyl)propionic acid; 3-hydroxy-L-tyrosine; Levodopa | 59-92-7 | C9H11NO4 | 详情 | 详情 |
| (II) | 29568 | methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate | C10H13NO4 | 详情 | 详情 | |
| (III) | 61955 | methyl (2S)-2-amino-3-[3,4-bis(acetyloxy)phenyl]propanoate | C14H17NO6 | 详情 | 详情 | |
| (IV) | 61956 | methyl (2S)-3-[3,4-bis(acetyloxy)phenyl]-2-isocyanatopropanoate | C15H15NO7 | 详情 | 详情 | |
| (V) | 61957 | (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide | C14H15N3O5 | 详情 | 详情 | |
| (VI) | 61958 | methyl (2S)-3-[3,4-bis(acetyloxy)phenyl]-2-[({5-[(E)-2-cyano-3-(diethylamino)-3-oxo-1-propenyl]-2-hydroxy-3-nitrophenoxy}carbonyl)amino]propanoate | C29H30N4O12 | 详情 | 详情 |