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【结 构 式】 
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【分子编号】19115 【品名】[(chlorocarbonyl)oxy](methoxy)methane 【CA登记号】 |
【 分 子 式 】C3H5ClO3 【 分 子 量 】124.5236 【元素组成】C 28.94% H 4.05% Cl 28.47% O 38.55% |
合成路线1
该中间体在本合成路线中的序号：(X)Nitrophenoxyacetate (III) (prepared from 2-nitrophenol (I) and tert-butyl bromoacetate), was reduced with H2 in the presence of Pd/C to give aniline (IV). This was condensed with Z-D-Phe (V) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (EDC) and 1-hydroxybenzotriazole (HOBt) to yield amide (VI), which was deprotected to amine (VII) by hydrogenolysis in the presence of Pd/C. Subsequent coupling with Z-Pro (VIII), followed by hydrogenolytic deprotection produced (IX). This was coupled with methyl oxalyl chloride (X) to afford (XI). Then, treatment with trifluoroacetic acid in CH2Cl2 gave acid (XII). Finally, dipeptide (XV) (obtained by coupling of protected 3-amino-2-hydroxy-4-phenylbutyric acid (XIII) with tert-butyl prolinamide (XIV)), was condensed with acid (XII) to produce the title compound.
| 【1】 Asagarasu, A.; et al.; Synthesis of dipeptide-type human immunodeficiency virus (HIV) protease inhibitors with a binding unit to GP120. Chem Pharm Bull 1998, 46, 5, 867. |
| 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) | 19106 | 2-nitrophenol | 88-75-5 | C6H5NO3 | 详情 | 详情 |
| (II) | 17430 | 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate | 5292-43-3 | C6H11BrO2 | 详情 | 详情 |
| (III) | 19108 | tert-butyl 2-(2-nitrophenoxy)acetate | C12H15NO5 | 详情 | 详情 | |
| (IV) | 19109 | tert-butyl 2-(2-aminophenoxy)acetate | C12H17NO3 | 详情 | 详情 | |
| (V) | 19110 | (2R)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropionic acid | C17H17NO4 | 详情 | 详情 | |
| (VI) | 19111 | tert-butyl 2-[2-[((2R)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropanoyl)amino]phenoxy]acetate | C29H32N2O6 | 详情 | 详情 | |
| (VII) | 19112 | tert-butyl 2-(2-[[(2R)-2-amino-3-phenylpropanoyl]amino]phenoxy)acetate | C21H26N2O4 | 详情 | 详情 | |
| (VIII) | 19113 | (2S)-1-[(benzyloxy)carbonyl]-2-pyrrolidinecarboxylic acid | 1148-11-4 | C13H15NO4 | 详情 | 详情 |
| (IX) | 19114 | tert-butyl 2-[2-[((2R)-3-phenyl-2-[[(2S)pyrrolidinylcarbonyl]amino]propanoyl)amino]phenoxy]acetate | C26H33N3O5 | 详情 | 详情 | |
| (X) | 19115 | [(chlorocarbonyl)oxy](methoxy)methane | C3H5ClO3 | 详情 | 详情 | |
| (XI) | 19116 | methyl 2-((2S)-2-[[((1R)-1-benzyl-2-[2-[2-(tert-butoxy)-2-oxoethoxy]anilino]-2-oxoethyl)amino]carbonyl]pyrrolidinyl)-2-oxoacetate | C29H35N3O8 | 详情 | 详情 | |
| (XII) | 19117 | 2-(2-[[(2R)-2-([[(2S)-1-(2-methoxy-2-oxoacetyl)pyrrolidinyl]carbonyl]amino)-3-phenylpropanoyl]amino]phenoxy)acetic acid | C25H27N3O8 | 详情 | 详情 | |
| (XIII) | 19118 | (2S,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutyric acid | C18H19NO5 | 详情 | 详情 | |
| (XIV) | 19119 | (2S)-N-(tert-butyl)-2-pyrrolidinecarboxamide | C9H18N2O | 详情 | 详情 | |
| (XV) | 19120 | (2S)-1-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl]-N-(tert-butyl)-2-pyrrolidinecarboxamide | C19H29N3O3 | 详情 | 详情 |