【结 构 式】 |
【分子编号】27033 【品名】ethyl 2-isopropyl-3-oxo-4-phenylbutanoate 【CA登记号】 |
【 分 子 式 】C15H20O3 【 分 子 量 】248.322 【元素组成】C 72.55% H 8.12% O 19.33% |
合成路线1
该中间体在本合成路线中的序号:(XI)The condensation of ethyl 2-bromo-3-methylbutyrate (IX) with phenylacetonitrile (X) by means of activated Zn in THF gives the ethyl 2-isopropyl-3-oxo-4-phenylbutyrate (XI), which is cyclized with thiourea (XII) by means of sodium ethoxide in refluxing ethanol yielding 6-benzyl-5-isopropyl-2-thioracil (XIII). The desulfurization of (XIII) with a refluxing solution of 10% chloroacetic acid in water affords the corresponding uracil (XIV), which is finally alkylated with chloromethyl ethyl ether (II) and BSA in chloroform.
【1】 Larsen, D.K.; et al.; Synthesis and potent anti-HIV-1 activity of novel 6-benzyluracil analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. J Med Chem 1996, 39, 12, 2427. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(II) | 13149 | 1-(Chloromethoxy)ethane; Chloromethyl ethyl ether | 3188-13-4 | C3H7ClO | 详情 | 详情 |
(IX) | 27032 | 2-Bromoisovalerianic acid ethyl ester; ethyl 2-bromo-3-methylbutanoate | 609-12-1 | C7H13BrO2 | 详情 | 详情 |
(X) | 17046 | Phenylacetonitrile; 2-phenylacetonitrile; Benzyl cyanide | 140-29-4 | C8H7N | 详情 | 详情 |
(XI) | 27033 | ethyl 2-isopropyl-3-oxo-4-phenylbutanoate | C15H20O3 | 详情 | 详情 | |
(XII) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
(XIII) | 27034 | 6-benzyl-5-isopropyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C14H16N2OS | 详情 | 详情 | |
(XIV) | 27035 | 6-benzyl-5-isopropyl-2,4(1H,3H)-pyrimidinedione | C14H16N2O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(III)The reaction of 2-phenylacetonitrile (I) with 2-bromo-3-methylbutyric acid ethyl ester (II) by means of Zn in THF gives the ketoester (III), which is cyclized with thiourea (IV) by means of sodium ethoxide in ethanol yielding 6-benzyl-5-isopropyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally, this compound is treated with chloromethyl methyl sulfide (VI) and K2CO3 in DMF.
【1】 Vig, R.; Mao, C.; Venkatachalam, T.K.; Tuel-Ahlgren, L.; Sudbeck, E.A.; Uckun, F.M.; 5-Alkyl-2-[(methylthiomethyl)thio]-6-(benzyl)-pyrimidin-4-(1H)-ones as potent non-nucleoside reverse transcriptase inhibitors of S-DABO series. Bioorg Med Chem Lett 1998, 8, 12, 1461. |
【2】 Sudbeck, E.A.; Mao, C.; Vig, R.; Venkatachalam, T.K.; Tuel-Ahlgren, L.; Uckun, F.M.; Structure-based design of novel dihydroalkoxybenzyloxopyrimidine derivatives as potent nonnucleoside inhibitors of the human immunodeficiency virus reverse transcriptase. Antimicrob Agents Chemother 1998, 42, 12, 3225. |
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) | 17046 | Phenylacetonitrile; 2-phenylacetonitrile; Benzyl cyanide | 140-29-4 | C8H7N | 详情 | 详情 |
(II) | 27032 | 2-Bromoisovalerianic acid ethyl ester; ethyl 2-bromo-3-methylbutanoate | 609-12-1 | C7H13BrO2 | 详情 | 详情 |
(III) | 27033 | ethyl 2-isopropyl-3-oxo-4-phenylbutanoate | C15H20O3 | 详情 | 详情 | |
(IV) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
(V) | 27034 | 6-benzyl-5-isopropyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C14H16N2OS | 详情 | 详情 | |
(VI) | 27701 | chloro(methylsulfanyl)methane | 2373-51-5 | C2H5ClS | 详情 | 详情 |