2,6-dichlorobenzoic acid -Drug Synthesis Database

【结构式】

【分子编号】41964

【品名】2,6-dichlorobenzoic acid

【CA登记号】50-30-6

【分子式】C₇H₄Cl₂O₂

【分子量】191.01296

【元素组成】C 44.02% H 2.11% Cl 37.12% O 16.75%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

Coupling of N-benzylpyroglutamic acid (I) with 4-nitrophenylalanine methyl ester (II) by means of O-benzotriazolyl-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HBTU) produced amide (III). After stannous chloride mediated reduction of the nitro group of (III), the resulting aniline (IV) was coupled with 2,6-dichlorobenzoic acid (V) to give diamide (VI). The title carboxylic acid was then obtained by ester hydrolysis with NaOH.

参考文献中间体

合成目标

【1】 Guthrie, R.W.; Chen, L.; Tilley, J.W.; et al.; N-Benzylpyroglutamyl-L-phenylanine derivatives as VCAM/VLA-4 antagonists. Bioorg Med Chem Lett 2000, 10, 8, 729.

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)	41961	1-benzyl-5-oxoproline		C₁₂H₁₃NO₃	详情	详情
(II)	15342	methyl (2S)-2-amino-3-(4-nitrophenyl)propanoate		C₁₀H₁₂N₂O₄	详情	详情
(III)	41962	methyl (2S)-2-[[(1-benzyl-5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-(4-nitrophenyl)propanoate		C₂₂H₂₃N₃O₆	详情	详情
(IV)	41963	methyl (2S)-3-(4-aminophenyl)-2-[[(1-benzyl-5-oxo-2-pyrrolidinyl)carbonyl]amino]propanoate		C₂₂H₂₅N₃O₄	详情	详情
(V)	41964	2,6-dichlorobenzoic acid	50-30-6	C₇H₄Cl₂O₂	详情	详情
(VI)	41965	methyl (2S)-2-[[(1-benzyl-5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-[4-[(2,6-dichlorobenzoyl)amino]phenyl]propanoate		C₂₉H₂₇Cl₂N₃O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVIII)

The methyl ester group of (XIV) was then hydrolyzed with NaOH, and the resulting carboxylic acid (XV) was activated as the mixed anhydride (XVI) with isobutyl chloroformate. Addition of diazomethane to anhydride (XVI) followed by treatment of the intermediate diazo ketone with HBr gave the bromo ketone (XVII). The bromide group of (XVII) was then displaced with 2,6-dichlorobenzoic acid (XVIII) to produce the dichlorobenzoate ester (XIX). The tert-butyl ester group of (XIX) was finally cleaved by treatment with trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Chung, H.-H.; Park, M.-J.; Min, C.-H.; Kang, C.-Y.; Park, T.-K.; Chang, H.-K.; Lee, T.-H.; Moon, K.-Y.; Kim, E.E.-K.; Oh, Y.-L.; Kim, Y.-M. (LG Chem Ltd.); Caspase inhibitor. WO 0121599; WO 0121600 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIV)	48033	4-(tert-butyl) 1-methyl (2S)-2-[([5-benzyl-3-[(1S)-2-methyl-1-(1-naphthoylamino)propyl]-4,5-dihydro-5-isoxazolyl]carbonyl)amino]butanedioate		C₃₅H₄₁N₃O₇	详情	详情
(XV)	48034	(2S)-2-[([5-benzyl-3-[(1S)-2-methyl-1-(1-naphthoylamino)propyl]-4,5-dihydro-5-isoxazolyl]carbonyl)amino]-4-(tert-butoxy)-4-oxobutyric acid		C₃₄H₃₉N₃O₇	详情	详情
(XVI)	48035			C₃₉H₄₇N₃O₉	详情	详情
(XVII)	48036	tert-butyl (3S)-3-[([5-benzyl-3-[(1S)-2-methyl-1-(1-naphthoylamino)propyl]-4,5-dihydro-5-isoxazolyl]carbonyl)amino]-5-bromo-4-oxopentanoate		C₃₅H₄₀BrN₃O₆	详情	详情
(XVIII)	41964	2,6-dichlorobenzoic acid	50-30-6	C₇H₄Cl₂O₂	详情	详情
(XIX)	48037	(3S)-3-[([5-benzyl-3-[(1S)-2-methyl-1-(1-naphthoylamino)propyl]-4,5-dihydro-5-isoxazolyl]carbonyl)amino]-5-(tert-butoxy)-2,5-dioxopentyl 2,6-dichlorobenzoate		C₄₂H₄₃Cl₂N₃O₈	详情	详情

Extended Information