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【结 构 式】 
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【分子编号】48037 【品名】(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 【CA登记号】 |
【 分 子 式 】C42H43Cl2N3O8 【 分 子 量 】788.72424 【元素组成】C 63.96% H 5.5% Cl 8.99% N 5.33% O 16.23% |
合成路线1
该中间体在本合成路线中的序号：(XIX)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.
| 【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 |