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【结 构 式】 
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【分子编号】61626 【品名】(E)-2-isopropyl-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-propenoic acid 【CA登记号】 |
【 分 子 式 】C17H24O5 【 分 子 量 】308.37456 【元素组成】C 66.21% H 7.84% O 25.94% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation of benzaldehyde (I) with ethyl isovalerate (II) by means of hexyl lithium and DIA in THF gives the hydroxyester (III), which is acylated with Ac2O and DMAP in THF to yield the acetoxy derivate (IV). The elimination reaction in (IV) by means of t-BuOK in THF affords the unsaturated ester (V), which is hydrolyzed with KOH in ethanol to provide the unsaturated free acid (VI). Finally, this compound is enantioselectively reduced with H2 over several chiral Rh catalysts {[Rh(NBD)2BF4, [Rh(NBD)(OCOCF3)2], [Rh(NBD)Cl2], etc} to give the target intermediate 2(R)-isopropyl-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]propionic acid (VII). (see scheme 26758001a, intermediate (VII)).
| 【1】 Herold, P.; Stutz, S. (Speedel Pharma Inc.); Preparation of (R)-2-alkyl-3-phenylpropionic acids. WO 0202500 . |
| 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) | 61620 | 4-Methoxy-3-(3-methoxypropoxy)benzaldehyde | 172900-75-3 | C12H16O4 | 详情 | 详情 |
| (II) | 61621 | propyl 3-methylbutanoate | C8H16O2 | 详情 | 详情 | |
| (III) | 61622 | propyl 2-{hydroxy[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutanoate | C20H32O6 | 详情 | 详情 | |
| (IV) | 61623 | propyl 2-{(acetyloxy)[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutanoate | C22H34O7 | 详情 | 详情 | |
| (V) | 61624 | propyl (E)-2-isopropyl-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-propenoate | C20H30O5 | 详情 | 详情 | |
| (VI) | 61626 | (E)-2-isopropyl-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-propenoic acid | C17H24O5 | 详情 | 详情 | |
| (VII) | 28119 | (2R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyric acid | C17H26O5 | 详情 | 详情 |