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【结 构 式】 
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【分子编号】45025 【品名】ethyl (3S)-3-([2-[(3S,5R)-3-amino-5-methyl-2-oxopyrrolidinyl]acetyl]amino)-4-pentynoate 【CA登记号】 |
【 分 子 式 】C14H21N3O4 【 分 子 量 】295.33856 【元素组成】C 56.94% H 7.17% N 14.23% O 21.67% |
合成路线1
该中间体在本合成路线中的序号：(XXI)Pyrrolidinone (X) was alkylated with ethyl bromoacetate to afford ester (XVII), which was further hydrolyzed to acid (XVIII). Its coupling with amino ester (XIX) in the presence of EDC and HOBt furnished amide (XX). The N-Boc group of (XX) was then cleaved with HCl in EtOAc to provide amine (XXI) Aldehyde (XXVI) was obtained by condensation of 2-aminopyridine-3-carboxaldehyde (XXII) with pyruvaldehyde dimethyl acetal (XXIII), followed by partial hydrogenation of the resulting naphthyridine (XXIV) and acid hydrolysis of the dimethyl acetal group. Finally, reductive condensation of amine (XXI) with aldehyde (XXVI) in the presence of sodium triacetoxyborohydride yielded the title compound.
| 【2】 Duggan, M.E.; Hartman, G.D.; Hoffman, W.F.; Meissner, R.S.; Perkins, J.J.; Askew, B.C.; Coleman, P.J.; Hutchinson, J.H.; Naylor-Olsen, A.M. (Merck & Co., Inc.); Integrin antagonists. EP 0934305; US 5981546; WO 9808840 . |
| 【1】 Nakanishi, T.; Otsuka, T.; Hashimoto, S.; Okamoto, M.; Muramatsu, Y.; Hino, M.; Hatanaka, H.; WF14865A and B, new cathepsins B and L inhibitors produed by Aphanoascus fulvescens. I. Taxomy, production, purification and biological properties. J Antibiot 2000, 53, 5, 449. |
| 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) | 45015 | tert-butyl (3S,5R)-5-methyl-2-oxopyrrolidinylcarbamate | C10H18N2O3 | 详情 | 详情 | |
| (XVII) | 45022 | ethyl 2-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methyl-2-oxopyrrolidinyl]acetate | C14H24N2O5 | 详情 | 详情 | |
| (XVIII) | 45023 | 2-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methyl-2-oxopyrrolidinyl]acetic acid | C12H20N2O5 | 详情 | 详情 | |
| (XIX) | 16297 | ethyl (3S)-3-amino-4-pentynoate | C7H11NO2 | 详情 | 详情 | |
| (XX) | 45024 | ethyl (3S)-3-[(2-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methyl-2-oxopyrrolidinyl]acetyl)amino]-4-pentynoate | C19H29N3O6 | 详情 | 详情 | |
| (XXI) | 45025 | ethyl (3S)-3-([2-[(3S,5R)-3-amino-5-methyl-2-oxopyrrolidinyl]acetyl]amino)-4-pentynoate | C14H21N3O4 | 详情 | 详情 | |
| (XXII) | 45026 | C6H6N2O | 详情 | 详情 | ||
| (XXIII) | 25433 | 1,1-dimethoxyacetone | 6342-56-9 | C5H10O3 | 详情 | 详情 |
| (XXIV) | 45027 | methoxy([1,8]naphthyridin-2-yl)methyl methyl ether; 2-(dimethoxymethyl)[1,8]naphthyridine | C11H12N2O2 | 详情 | 详情 | |
| (XXV) | 45028 | methoxy(5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)methyl methyl ether; 7-(dimethoxymethyl)-1,2,3,4-tetrahydro[1,8]naphthyridine | C11H16N2O2 | 详情 | 详情 | |
| (XXVI) | 45029 | 5,6,7,8-tetrahydro[1,8]naphthyridine-2-carbaldehyde | C9H10N2O | 详情 | 详情 |