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【结 构 式】

【分子编号】52032

【品名】(2-ethoxy-2-oxoethyl)(triphenyl)phosphonium chloride

【CA登记号】

【 分 子 式 】C22H22ClO2P

【 分 子 量 】384.841942

【元素组成】C 68.66% H 5.76% Cl 9.21% O 8.31% P 8.05%

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:(V)

2,3-Dichloro-4-hydroxybenzaldehyde (I) was converted to the corresponding aryl triflate (II), which was subsequently condensed with 2-bromothiophenol (III), yielding the diaryl sulfide (IV). Wittig reaction of aldehyde (IV) with the ylide resulting from the phosphonium salt (V) afforded the unsaturated ester (VI). Cycloaddition between (VI) and the in situ-generated dimethylsulfoxonium methylide gave rise to the cyclopropane derivative (VII). After basic hydrolysis of the ethyl ester (VII), the resultant carboxylic acid (VIII) was coupled with 1-(3-aminopropyl)-2-pyrrolidinone (IX), providing amide (X). Displacement of the aryl bromide group of (X) with ethyl nipecotate (XI) in the presence of BINAP and Pd catalysts furnished the piperidine-substituted compound (XII). The ethyl ester group of (XII) was finally hydrolyzed to the target carboxylic acid under basic conditions.

1 Link, J.T.; et al.; Discovery and SAR of diarylsulfide cyclopropylamide LFA-1/ICAM-1 interaction antagonists. Bioorg Med Chem Lett 2001, 11, 8, 973.
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) 52028 2,3-dichloro-4-hydroxybenzaldehyde C7H4Cl2O2 详情 详情
(II) 52029 2,3-dichloro-4-formylphenyl trifluoromethanesulfonate C8H3Cl2F3O4S 详情 详情
(III) 52030 2-Bromobenzenethiol; 2-Bromothiophenol;2-bromo-benzenethio;2-Bromo thiophenol 6320-02-1 C6H5BrS 详情 详情
(IV) 52031 4-[(2-bromophenyl)sulfanyl]-2,3-dichlorobenzaldehyde C13H7BrCl2OS 详情 详情
(V) 52032 (2-ethoxy-2-oxoethyl)(triphenyl)phosphonium chloride C22H22ClO2P 详情 详情
(VI) 52033 ethyl (E)-3-[4-[(2-bromophenyl)sulfanyl]-2,3-dichlorophenyl]-2-propenoate C17H13BrCl2O2S 详情 详情
(VII) 52034 ethyl (1S,2R)-2-[4-[(2-bromophenyl)sulfanyl]-2,3-dichlorophenyl]cyclopropanecarboxylate C18H15BrCl2O2S 详情 详情
(VIII) 52035 (1S,2R)-2-[4-[(2-bromophenyl)sulfanyl]-2,3-dichlorophenyl]cyclopropanecarboxylic acid C16H11BrCl2O2S 详情 详情
(IX) 52036 N-(3-Aminopropyl)-2-pyrrolidinone; N-(3'-Aminopropyl)-2-pyrrolidinone 7663-77-6 C7H14N2O 详情 详情
(X) 52037 (1S,2R)-2-[4-[(2-bromophenyl)sulfanyl]-2,3-dichlorophenyl]-N-[3-(2-oxo-1-pyrrolidinyl)propyl]cyclopropanecarboxamide C23H23BrCl2N2O2S 详情 详情
(XI) 25693 ethyl 3-piperidinecarboxylate 5006-62-2 C8H15NO2 详情 详情
(XII) 52038 ethyl 1-[2-([2,3-dichloro-4-[(1R,2S)-2-([[3-(2-oxo-1-pyrrolidinyl)propyl]amino]carbonyl)cyclopropyl]phenyl]sulfanyl)phenyl]-3-piperidinecarboxylate C31H37Cl2N3O4S 详情 详情
Extended Information