methyl 1-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】53416

【品名】methyl 1-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylate

【CA登记号】n/a

【分子式】C₂₄H₂₂N₂O₅

【分子量】418.44916

【元素组成】C 68.89% H 5.3% N 6.69% O 19.12%

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：(XXX)

N-Phthaloyl-L-phenylalanine (X) is coupled to the racemic unsaturated amine (XXVIII) by means of EEDQ in dichloromethane to provide amide (XXIX), which is converted into a mixture of diastereomeric amides (XXX) by ozonolysis in CH2Cl2/MeOH, followed by reduction with dimethyl sulfide in pyridine and dehydration with TFA in refluxing CH2Cl2. Finally, chromatographic separation of this mixture by HPLC yields the previously described intermediate (XII).

参考文献中间体

合成目标

【1】 del Fresno, M.; Bayes, M.; Castaner, R.M.; Sorbera, L.A.; MDL-100240. Drugs Fut 2002, 27, 5, 458.
【2】 Flynn, G.A.; et al.; An acyl-iminium ion cyclization route to a novel conformationally restricted dipeptide mimic: Applications to angiotensin-converting enzyme inhibition. J Am Chem Soc 1987, 109, 7914.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	37293	(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropionic acid	5123-55-7	C₁₇H₁₃NO₄	详情	详情
(XII)	37296	methyl (2S)-1-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylate		C₂₄H₂₂N₂O₅	详情	详情
(XXVIII)	49791	2-chloro-2-cyclohexen-1-ylamine; 2-chloro-2-cyclohexen-1-amine		C₆H₁₀ClN	详情	详情
(XXIX)	53415	(2S)-N-(2-chloro-2-cyclohexen-1-yl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanamide	n/a	C₂₃H₂₁ClN₂O₃	详情	详情
(XXX)	53416	methyl 1-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylate	n/a	C₂₄H₂₂N₂O₅	详情	详情

Extended Information