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【结 构 式】

【分子编号】16630

【品名】methyl 4-(2,4-dihydroxy-3-propylphenyl)-2,4-dioxobutanoate

【CA登记号】

【 分 子 式 】C14H16O6

【 分 子 量 】280.27744

【元素组成】C 60% H 5.75% O 34.25%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

The Eastern fragment (XIV) was derived from 2',4'-dihydroxy-3'-propylacetophenone (VII). This material could be converted into (X) using identical procedures to those developed in house for the synthesis of SC-41930. (X) was resolved into its two homochiral components using enzymatic methods (Amano lipase AK, pH 7.4 buffer followed by selective methylation [CH3l, KHCO3, DMSO] and recrystallization. The overall yield for this process was 33% [based on a resolution yield of 40%]) and afforded the desired (-)-isomer (XII) in > 99% e.e. This material was silylated (TBDMS chloride, DMF, imidazole) and reduced to the primary carbinol with DIBAL-H. Conversion to the Eastern fragment (XIV) was accomplished by an efficient 3-step process involving triflation (Tf2O, CH2Cl2), homologation with lithium tert-butyl acetate and protective group removal/transesterification with ethanolic hydrogen chloride (92% for the three steps). The overall yield of Eastern fragment (> 99% e.e.) was 17% based on 2',4'-dihydroxy-3'-propylacetophenone (VII) as starting material.

1 Smith, P.F.; Paulson, S.K.; Tsai, B.S.; Fretland, D.J.; Dygos, J.H.; Yu, S.S.; Djuric, S.W.; SC-53228. Drugs Fut 1994, 19, 12, 1093.
2 Yu, S.; Docter, S.; Djuric, S.; et al.; Synthesis and pharmacological activity of SC-53228, a leukotriene B4 receptor antagonist with high intrinsic potency and selectivity. Bioorg Med Chem Lett 1994, 4, 6, 811-6.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 13137 2',4'-Dihydroxy-3'-propylacetophenone; 1-(2,4-Dihydroxy-3-propylphenyl)-1-ethanone 40786-69-4 C11H14O3 详情 详情
(VIII) 16630 methyl 4-(2,4-dihydroxy-3-propylphenyl)-2,4-dioxobutanoate C14H16O6 详情 详情
(IX) 16631 methyl 7-hydroxy-4-oxo-8-propyl-4H-chromene-2-carboxylate C14H14O5 详情 详情
(X) 16632 methyl 7-hydroxy-8-propyl-2-chromanecarboxylate C14H18O4 详情 详情
(XI) 16633 7-hydroxy-8-propyl-2-chromanecarboxylic acid C13H16O4 详情 详情
(XII) 16632 methyl 7-hydroxy-8-propyl-2-chromanecarboxylate C14H18O4 详情 详情
(XIII) 16635 (7-[[tert-butyl(dimethyl)silyl]oxy]-8-propyl-3,4-dihydro-2H-chromen-2-yl)methanol C19H32O3Si 详情 详情
(XIV) 16636 ethyl 3-(7-hydroxy-8-propyl-3,4-dihydro-2H-chromen-2-yl)propanoate C17H24O4 详情 详情
Extended Information