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【结 构 式】

【分子编号】29644

【品名】methyl 3-[(1S)-1-([4-[(2-amino-6-methyl-4-oxo-3,4-dihydro-5-quinazolinyl)sulfanyl]benzoyl]amino)-2-methoxy-2-oxoethyl]benzoate

【CA登记号】

【 分 子 式 】C27H24N4O6S

【 分 子 量 】532.57692

【元素组成】C 60.89% H 4.54% N 10.52% O 18.02% S 6.02%

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:(VII)

Strecker condensation of 3-cyanobenzaldehyde (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 groups 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 both methyl esters of (VII) afforded the target dicarboxylate salt.

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) 13245 3-Formylbenzonitrile; 3-Cyanobenzaldehyde 24964-64-5 C8H5NO 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) 29641 3-((S)-cyano[[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)benzonitrile C17H15N3O 详情 详情
(IV) 29642 3-[(S)-amino(carboxy)methyl]benzoic acid C9H9NO4 详情 详情
(V) 29643 methyl 3-[(1S)-1-amino-2-methoxy-2-oxoethyl]benzoate C11H13NO4 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) 29644 methyl 3-[(1S)-1-([4-[(2-amino-6-methyl-4-oxo-3,4-dihydro-5-quinazolinyl)sulfanyl]benzoyl]amino)-2-methoxy-2-oxoethyl]benzoate C27H24N4O6S 详情 详情
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