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【结 构 式】 
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【分子编号】29512 【品名】ethyl 2-amino-4-methyl-3-thiophenecarboxylate 【CA登记号】43088-42-2 |
【 分 子 式 】C8H11NO2S 【 分 子 量 】185.24688 【元素组成】C 51.87% H 5.99% N 7.56% O 17.27% S 17.31% |
合成路线1
该中间体在本合成路线中的序号：(I)The coupling of 2-amino-4-methylthiophene-3-carboxylic acid ethyl ester (I) with N-(tert-butoxycarbonyl)-L-alanine (II) by means of isobutyl chloroformate and NMM, followed by cyclization with triphenylphosphine in CCl4 gives the thieno-oxazinone (III), which is deprotected with TFA yielding (IV) with a free amino group that is acylated with cinnamic acid by means of DEC and DIEA.
| 【1】 Tew, D.G.; Pinto, I.L.S.M.; Jarvest, R.L.; Jennings, L.J.; Dabrowski, C.E.; Fernandez, A.V.; Lavery, P.; Inhibition of herpes proteases and antiviral activity of 2-substituted thieno[2,3-d]oxazinones. Bioorg Med Chem Lett 1999, 9, 3, 443. |
| 【2】 Jarvest, R.L.; Jennings, L.J.A.; Pinto, I.L. (SmithKline Beecham plc); Thienoxazinone derivs. useful as antiviral agents. WO 9727200 . |
| 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) | 29512 | ethyl 2-amino-4-methyl-3-thiophenecarboxylate | 43088-42-2 | C8H11NO2S | 详情 | 详情 |
| (II) | 26450 | Boc-L-Alanine;(S)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-Boc-L-alanine; (2S)-2-[(tert-butoxycarbonyl)amino]propionic acid | 15761-38-3 | C8H15NO4 | 详情 | 详情 |
| (III) | 28659 | tert-butyl (1S)-1-(5-methyl-4-oxo-4H-thieno[2,3-d][1,3]oxazin-2-yl)ethylcarbamate | C14H18N2O4S | 详情 | 详情 | |
| (IV) | 28660 | 2-[(1S)-1-aminoethyl]-5-methyl-4H-thieno[2,3-d][1,3]oxazin-4-one | C9H10N2O2S | 详情 | 详情 | |
| (V) | 10449 | (Z)-3-Phenyl-2-propenoic acid | 621-82-9 | C9H8O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The coupling of 2-amino-4-methylthiophene-3-carboxylic acid ethyl ester (I) with N-(tert-butoxycarbonyl)-L-alanine (II) by means of isobutyl chloroformate and NMM, followed by cyclization with triphenylphosphine in CCl4 gives the thieno-oxazinone (III), which is deprotected with TFA yielding (IV) with a free amino group that is acylated with 3-(5-bromothien-2-yl)-2(E)-propenoic acid by means of DEC and DIEA.
| 【1】 Tew, D.G.; Pinto, I.L.S.M.; Jarvest, R.L.; Jennings, L.J.; Dabrowski, C.E.; Fernandez, A.V.; Lavery, P.; Inhibition of herpes proteases and antiviral activity of 2-substituted thieno[2,3-d]oxazinones. Bioorg Med Chem Lett 1999, 9, 3, 443. |
| 【2】 Jarvest, R.L.; Jennings, L.J.A.; Pinto, I.L. (SmithKline Beecham plc); Thienoxazinone derivs. useful as antiviral agents. WO 9727200 . |
| 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) | 29512 | ethyl 2-amino-4-methyl-3-thiophenecarboxylate | 43088-42-2 | C8H11NO2S | 详情 | 详情 |
| (II) | 26450 | Boc-L-Alanine;(S)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-Boc-L-alanine; (2S)-2-[(tert-butoxycarbonyl)amino]propionic acid | 15761-38-3 | C8H15NO4 | 详情 | 详情 |
| (III) | 28659 | tert-butyl (1S)-1-(5-methyl-4-oxo-4H-thieno[2,3-d][1,3]oxazin-2-yl)ethylcarbamate | C14H18N2O4S | 详情 | 详情 | |
| (IV) | 28660 | 2-[(1S)-1-aminoethyl]-5-methyl-4H-thieno[2,3-d][1,3]oxazin-4-one | C9H10N2O2S | 详情 | 详情 | |
| (V) | 29513 | (E)-3-(5-bromo-2-thienyl)-2-propenoic acid | C7H5BrO2S | 详情 | 详情 |