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【结 构 式】 
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【分子编号】28352 【品名】3-(3,5-dichlorophenyl)-beta-alanine 【CA登记号】 |
【 分 子 式 】C9H9Cl2NO2 【 分 子 量 】234.0814 【元素组成】C 46.18% H 3.88% Cl 30.29% N 5.98% O 13.67% |
合成路线1
该中间体在本合成路线中的序号：(II)The reaction of 3,5-dichlorobenzaldehyde (I) with malonic acid and ammonium acetate in refluxing isopropanol gives 3-amino-3-(3,5-dichlorophenyl)propionic acid (II), which is esterified with ethanol and HCl yielding the ethyl ester (III), The condensation of (III) with N-(tert-butoxycarbonyl)glycine succinimidyl ester (IV) by means of TEA in THF affords the glycinamide (V), which is deprotected with HCl in dioxane to afford intermediate (VI). The free amino group of (VI) is then acylated with 3-guanidinobenzoic acid by means of isobutyl chloroformate and NMM in DMF yielding the ethyl ester (VIII) of the target product, which is finally hydrolyzed with LiOH in water.
| 【1】 Ruminski, P.G.; Clare, M.; Collins, P.W.; Desai, B.N.; Lindmark, R.J.; Rico, J.G.; Rogers, T.E.; Russell, M.A. (Pharmacia Corp.); Meta-guanidine, urea, thiourea or azacyclic amino benzoic acid derivs. as integrin antagonists. EP 0850221; JP 1999510814; US 6013651; WO 9708145 . |
| 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) | 24169 | 3,5-dichlorobenzaldehyde | 10203-08-4 | C7H4Cl2O | 详情 | 详情 |
| (II) | 28352 | 3-(3,5-dichlorophenyl)-beta-alanine | C9H9Cl2NO2 | 详情 | 详情 | |
| (III) | 28353 | ethyl 3-amino-3-(3,5-dichlorophenyl)propanoate | C11H13Cl2NO2 | 详情 | 详情 | |
| (IV) | 16364 | tert-butyl N-[2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl]carbamate; N-T-BOC-glycine N-hydroxysuccinimide ester | 3392-07-2 | C11H16N2O6 | 详情 | 详情 |
| (V) | 28354 | ethyl 3-([2-[(tert-butoxycarbonyl)amino]acetyl]amino)-3-(3,5-dichlorophenyl)propanoate | C18H24Cl2N2O5 | 详情 | 详情 | |
| (VI) | 28355 | ethyl 3-[(2-aminoacetyl)amino]-3-(3,5-dichlorophenyl)propanoate | C13H16Cl2N2O3 | 详情 | 详情 | |
| (VII) | 28356 | 3-[[amino(imino)methyl]amino]benzoic acid | C8H9N3O2 | 详情 | 详情 | |
| (VIII) | 28357 | ethyl 3-([2-[(3-[[amino(imino)methyl]amino]benzoyl)amino]acetyl]amino)-3-(3,5-dichlorophenyl)propanoate | C21H23Cl2N5O4 | 详情 | 详情 |