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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information