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【结 构 式】 
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【分子编号】36599 【品名】tert-butyl (1S)-1-([[(1S)-2-[((1S)-2-(1,3-benzothiazol-2-yl)-1-[[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]methyl]-2-hydroxyethyl)amino]-1-(4-fluorobenzyl)-2-oxoethyl]amino]carbonyl)-2-methylpropylcarbamate 【CA登记号】 |
【 分 子 式 】C42H52FN5O8S 【 分 子 量 】805.9681832 【元素组成】C 62.59% H 6.5% F 2.36% N 8.69% O 15.88% S 3.98% |
合成路线1
该中间体在本合成路线中的序号：(IX)Oxidation of aldehyde (I) by means of sodium chlorite gave carboxylic acid (II), which was converted to the corresponding Weinreb amide (III) via activation with isobutyl chloroformate and N-methylmorpholine. Subsequent condensation of (III) with 2-lithiobenzothiazole (IV) in cold THF formed the benzothiazolyl ketone (V). In order to minimize racemization, ketone (V) was reduced to alcohol (VI) using NaBH4. After deprotection of the Boc group of (VI) with HCl in dioxan, the resulting amino alcohol (VII) was coupled with the protected dipeptide (VIII) to furnish (IX). Further acid deprotection of the Boc group of (IX) afforded amine (X).
| 【1】 Zhou, R.; Dragovich, P.S.; Webber, S.E.; et al.; Structure-based design of ketone-containing, tripeptidyl human rhinovirus 3C protease inhibitors. Bioorg Med Chem Lett 2000, 10, 1, 45. |
| 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) | 32119 | tert-butyl (1S)-2-[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]-1-formylethylcarbamate | C21H30N2O6 | 详情 | 详情 | |
| (II) | 36592 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]propionic acid | C21H30N2O7 | 详情 | 详情 | |
| (III) | 36593 | tert-butyl (1S)-1-[[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]methyl]-2-[methoxy(methyl)amino]-2-oxoethylcarbamate | C23H35N3O7 | 详情 | 详情 | |
| (IV) | 36594 | 1,3-benzothiazol-2-yllithium | C7H4LiNS | 详情 | 详情 | |
| (V) | 36595 | tert-butyl (1S)-2-(1,3-benzothiazol-2-yl)-1-[[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]methyl]-2-oxoethylcarbamate | C28H33N3O6S | 详情 | 详情 | |
| (VI) | 36596 | tert-butyl (1S)-2-(1,3-benzothiazol-2-yl)-1-[[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]methyl]-2-hydroxyethylcarbamate | C28H35N3O6S | 详情 | 详情 | |
| (VII) | 36597 | (3S)-3-[(2S)-2-amino-3-(1,3-benzothiazol-2-yl)-3-hydroxypropyl]-1-(2,4-dimethoxybenzyl)-2-pyrrolidinone | C23H27N3O4S | 详情 | 详情 | |
| (VIII) | 36598 | (2S)-2-([(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoyl]amino)-3-(4-fluorophenyl)propionic acid | C19H27FN2O5 | 详情 | 详情 | |
| (IX) | 36599 | tert-butyl (1S)-1-([[(1S)-2-[((1S)-2-(1,3-benzothiazol-2-yl)-1-[[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]methyl]-2-hydroxyethyl)amino]-1-(4-fluorobenzyl)-2-oxoethyl]amino]carbonyl)-2-methylpropylcarbamate | C42H52FN5O8S | 详情 | 详情 | |
| (X) | 36600 | (2S)-2-amino-N-[(1S)-2-[((1S)-2-(1,3-benzothiazol-2-yl)-1-[[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]methyl]-2-hydroxyethyl)amino]-1-(4-fluorobenzyl)-2-oxoethyl]-3-methylbutanamide | C37H44FN5O6S | 详情 | 详情 |