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【结 构 式】 
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【分子编号】29640 【品名】methyl (2S)-2-([4-[(2-amino-6-methyl-4-oxo-3,4-dihydro-5-quinazolinyl)sulfanyl]benzoyl]amino)-2-(3-hydroxyphenyl)ethanoate 【CA登记号】 |
【 分 子 式 】C25H22N4O5S 【 分 子 量 】490.53964 【元素组成】C 61.21% H 4.52% N 11.42% O 16.31% S 6.54% |
合成路线1
该中间体在本合成路线中的序号：(VII)Strecker condensation of 3-hydroxybenzaldehyde (I) with trimethylsilyl cyanide in the presence of (S)-2-phenylglycine (II) yielded the chiral aminonitrile (III) as the major diastereoisomer. Oxidative cleavage of the chiral auxiliary of (III) with lead tetraacetate, followed by acid hydrolysis of the nitrile group provided the (S)-amino acid (IV), which was esterified with MeOH and Me3SiCl. The resulting aminoester (V) was coupled with carboxylic acid (VI) using diphenylphosphoryl azide to form amide ester (VII). Finally, saponification of the methyl ester of (VIII) afforded the target carboxylic acid.
| 【1】 Baek, D.-J.; Park, Y.-K.; Heo, H.I.; Lee, M.; Yang, Z.; Choi, M.; Synthesis of 5-substituted quinazolinone derivatives and their inhibitory activity in vitro. Bioorg Med Chem Lett 1998, 8, 23, 3287. |
| 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) | 28537 | 3-hydroxybenzaldehyde | 100-83-4 | C7H6O2 | 详情 | 详情 |
| (II) | 10973 | (2S)-2-Amino-2-phenyl-1-ethanol; (S)-2-Hydroxy-1-phenylethylamine; (S)-(+)-2-Phenylglycinol; (S)-2-Amino-2-phenyl-1-ethanol | 20989-17-7 | C8H11NO | 详情 | 详情 |
| (III) | 29636 | (2S)-2-(3-hydroxyphenyl)-2-[[(1R)-2-hydroxy-1-phenylethyl]amino]ethanenitrile | C16H16N2O2 | 详情 | 详情 | |
| (IV) | 29637 | (2S)-2-amino-2-(3-hydroxyphenyl)ethanoic acid | C8H9NO3 | 详情 | 详情 | |
| (V) | 29638 | methyl (2S)-2-amino-2-(3-hydroxyphenyl)ethanoate | C9H11NO3 | 详情 | 详情 | |
| (VI) | 29639 | 4-[(2-amino-6-methyl-4-oxo-3,4-dihydro-5-quinazolinyl)sulfanyl]benzoic acid | C16H13N3O3S | 详情 | 详情 | |
| (VII) | 29640 | methyl (2S)-2-([4-[(2-amino-6-methyl-4-oxo-3,4-dihydro-5-quinazolinyl)sulfanyl]benzoyl]amino)-2-(3-hydroxyphenyl)ethanoate | C25H22N4O5S | 详情 | 详情 |