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【结 构 式】 
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【分子编号】23620 【品名】tert-butyl (1S)-1-[[methoxy(methyl)amino]carbonyl]-3-phenylpropylcarbamate 【CA登记号】 |
【 分 子 式 】C17H26N2O4 【 分 子 量 】322.40452 【元素组成】C 63.33% H 8.13% N 8.69% O 19.85% |
合成路线1
该中间体在本合成路线中的序号：(II)N-Boc-Homophenylalanine (I) was coupled to N,O-dimethyl hydroxylamine using DCC, and the resulting N-methoxy amide (II) was reduced to aldehyde (III) with LiAlH4. Sulfonyl phosphonate (VI), (prepared from methyl phenyl sulfone (IV) and diethyl chlorophosphate (V)), was then condensed with aldehyde (III) in the presence of NaH to provide the vinylogous sulfone (VII). Subsequent acid deprotection of the Boc group of (VII) yielded amine (VIII). This was finally coupled with mixed anhydride (X), (obtained from morpholinocarbonyl-phenylalanine (IX) and isobutyl chloroformate in the presence of N-methylmorpholine), to furnish the target amide.
| 【1】 Rasnick, D.; Klaus, J.L.; Palmer, J.T. (Khepri Pharmaceuticals Inc.); Irreversible cysteine protease inhibitors containi. WO 9523222 . |
| 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) | 23619 | (2S)-2-[(tert-butoxycarbonyl)amino]-4-phenylbutyric acid | 100564-78-1 | C15H21NO4 | 详情 | 详情 |
| (II) | 23620 | tert-butyl (1S)-1-[[methoxy(methyl)amino]carbonyl]-3-phenylpropylcarbamate | C17H26N2O4 | 详情 | 详情 | |
| (III) | 23621 | tert-butyl (1S)-1-formyl-3-phenylpropylcarbamate | C15H21NO3 | 详情 | 详情 | |
| (IV) | 23622 | methyl phenyl sulfone; methyl(dioxo)phenyl-lambda(6)-sulfane | 3112-85-4 | C7H8O2S | 详情 | 详情 |
| (V) | 23623 | Chlorophosphoric acid ethyl ester；Phosphorochloridic acid diethyl ester；Diethyl chlorophosphate;diethyl phosphorochloridate | 814-49-3 | C4H10ClO3P | 详情 | 详情 |
| (VI) | 23624 | diethyl (phenylsulfonyl)methylphosphonate | C11H17O5PS | 详情 | 详情 | |
| (VII) | 23625 | tert-butyl (1S,2E)-1-phenethyl-3-(phenylsulfonyl)-2-propenylcarbamate | C22H27NO4S | 详情 | 详情 | |
| (VIII) | 23626 | (1S,2E)-1-phenethyl-3-(phenylsulfonyl)-2-propenylamine; (E,3S)-5-phenyl-1-(phenylsulfonyl)-1-penten-3-amine | C17H19NO2S | 详情 | 详情 | |
| (IX) | 23627 | (2S)-2-[(4-morpholinylcarbonyl)amino]-3-phenylpropionic acid | C14H18N2O4 | 详情 | 详情 | |
| (X) | 23628 | N-(4-Morpholinylcarbonyl)-L-phenylalanine ethoxycarbonyl anhydride | C17H22N2O6 | 详情 | 详情 |