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【结 构 式】 
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【分子编号】38734 【品名】2-methyl-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid 【CA登记号】 |
【 分 子 式 】C14H15NO5 【 分 子 量 】277.27684 【元素组成】C 60.64% H 5.45% N 5.05% O 28.85% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of 2-amino-2-methylglutaric acid (I) with phthalimide (II) by means of TEA in refluxing toluene gives 2-methyl-2-phthalimidoglutaric acid (II), which is partially reduced with Zn and acetic acid yielding the racemic indolinone derivative (IV). The esterification of (IV) affords the dimethyl ester (V), which is enantioselectively monohydrolyzed by means of ChiroCLEC-BL catalyst affording a mixture of the (S)-monoester (VI) and unchanged (R)-diester (R)-(V), which is separated by flash chromatography. Finally, the chiral monoester (VI) is hydrolyzed with HCl/AcOH.
| 【1】 Shah, J.H.; et al.; Synthesis and enantiomeric separation of 2-phthalimidino-glutaric acid analogues: Potent inhibitors of tumor metastasis. J Med Chem 1999, 42, 16, 3014. |
| 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) | 38732 | 2-methylglutamic acid | C6H11NO4 | 详情 | 详情 | |
| (II) | 12376 | Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione | 85-41-6 | C8H5NO2 | 详情 | 详情 |
| (III) | 38733 | 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-methylpentanedioic acid | C14H13NO6 | 详情 | 详情 | |
| (IV) | 38734 | 2-methyl-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid | C14H15NO5 | 详情 | 详情 | |
| (V) | 38735 | dimethyl 2-methyl-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioate | C16H19NO5 | 详情 | 详情 | |
| (VI) | 38736 | (2S)-5-methoxy-2-methyl-5-oxo-2-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)pentanoic acid | C15H17NO5 | 详情 | 详情 |