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【结 构 式】 
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【分子编号】45679 【品名】tert-butyl 3-[4-(4-[4-[(E)-3-(tert-butoxy)-3-oxo-1-propenyl]phenyl]-5-[4-[(E)-3-(hexadecylamino)-3-oxo-1-propenyl]phenyl]-1H-imidazol-2-yl)phenyl]-4,5-dihydro-5-isoxazolecarboxylate 【CA登记号】 |
【 分 子 式 】C55H72N4O6 【 分 子 量 】885.20004 【元素组成】C 74.63% H 8.2% N 6.33% O 10.84% |
合成路线1
该中间体在本合成路线中的序号：(XII)Heck reaction of 4,4'-dibromobenzil (VI) with tert-butyl acrylate (III) in the presence of palladium diacetate and tri(o-tolyl)phosphine afforded the arylacrylate ester (VII), which was subsequently condensed with the acrylamide (X) (prepared from acryloyl chloride (VIII) and hexadecylamine (IX)), to furnish adduct (XI). The condensation of diketone (XI) with aldehyde (V) in the presence of ammonium acetate in HOAc produced imidazole (XII). The tert-butyl ester groups of (XII) were finally cleaved by treatment with trifluoroacetic acid.
| 【1】 Slee, D.H.; et al.; Development of potent non-carbohydrate imidazole-based small molecule selectin inhibitors antiinflammatory activity. J Med Chem 2001, 44, 13, 2094. |
| 【2】 Kondo, H.; Inoue, Y.; Jones, T.K.; Ripka, W.C.; Yu, J.; Raheja, R.K.; Nguyen, T.N.; Slee, D.H. (NV Organon; Ontogen Corp.); Substd. thiazoles for treatment of human diseases involving modulators of P-, L- and E-selectin. WO 0033836; WO 0034255 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 12760 | tert-butyl acrylate | 1663-39-4 | C7H12O2 | 详情 | 详情 |
| (V) | 45678 | tert-butyl (E)-3-[4-(2-[4-[(E)-3-(hexadecylamino)-3-oxo-1-propenyl]phenyl]-2-oxoacetyl)phenyl]-2-propenoate | C40H55NO5 | 详情 | 详情 | |
| (VI) | 38940 | 1,2-bis(4-bromophenyl)-1,2-ethanedione | 35578-47-3 | C14H8Br2O2 | 详情 | 详情 |
| (VII) | 45675 | tert-butyl (E)-3-[4-[2-(4-bromophenyl)-2-oxoacetyl]phenyl]-2-propenoate | C21H19BrO4 | 详情 | 详情 | |
| (VIII) | 11577 | Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride | 814-68-6 | C3H3ClO | 详情 | 详情 |
| (IX) | 45676 | 1-Aminohexadecane; n-Hexadecylamine; Palmitylamine; Cetylamine; hexadecylamine; 1-hexadecanamine | 143-27-1 | C16H35N | 详情 | 详情 |
| (X) | 45677 | N-hexadecylacrylamide | C19H37NO | 详情 | 详情 | |
| (XI) | 45674 | tert-butyl 3-(4-formylphenyl)-4,5-dihydro-5-isoxazolecarboxylate | C15H17NO4 | 详情 | 详情 | |
| (XII) | 45679 | tert-butyl 3-[4-(4-[4-[(E)-3-(tert-butoxy)-3-oxo-1-propenyl]phenyl]-5-[4-[(E)-3-(hexadecylamino)-3-oxo-1-propenyl]phenyl]-1H-imidazol-2-yl)phenyl]-4,5-dihydro-5-isoxazolecarboxylate | C55H72N4O6 | 详情 | 详情 |