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【结 构 式】

【分子编号】64700

【品名】 

【CA登记号】

【 分 子 式 】C12H10FN3O4

【 分 子 量 】279.2276232

【元素组成】C 51.62% H 3.61% F 6.8% N 15.05% O 22.92%

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:(XII)

2) The cyclization of 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid (IV) with KCN and ammonium carbonate in hot water (80-90 C) gives 6-fluoro-2',5'-dioxospiro[3,4-dihydro-2H-1-benzopyran-4,4'-imidazolidine]-2-carboxylic acid (X) as a (5:1)-mixture of the (RS,RS)- and (RS,SR)-diastereomers. This mixture is treated with SiCl4 and dry ammonia in pyridine, yielding the corresponding (5:1)-mixture of amides (XI), which is separated by recrystallization, affording the (RS,RS)-diastereomer (XII) as a pure compound. The optical resolution of (XII) with N-methylquininium hydroxide (XIII) and crystallization gives the (2S,4S)-isomer as the N-methylquininium salt (XIV), which is finally treated with 1N aqueous HCl in ethanol/water.

1 Mealy, N.; Castaner, J.; SNK-860. Drugs Fut 1996, 21, 3, 261.
2 Kurono, M.; Kondo, Y.; Yamaguchi, T.; Miura, K.; Usui, T.; Terada, N.; Asano, K.; Mizuno, K.; Matsubara, A.; Kato, N.; Sawai, K.; Unno, R.; Ozawa, H.; Fukushima, M. (Sanwa Kagaku Kenkyusho Co., Ltd.); Hydantoin derivs. for treating complications of diabetes. EP 0264586; JP 1988057588; JP 1988126881; JP 1988250373; US 4861792; US 4978758; US 5447946 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 16060 6-fluoro-4-oxo-2-chromanecarboxylic acid C10H7FO4 详情 详情
(X) 16067 6-Fluoro-2',5'-dioxo-3,4-dihydro-2H-spiro[1-benzopyran-4,4'-imidazolidin]-2-ylcarboxylic acid C12H9FN2O5 详情 详情
(XI) 16068 (rac)-(6-Fluoro-2',5'-dioxo-3,4-dihydro-2H-spiro[1-benzopyran-4,4'-imidazolidin]-2-ylcarboxamide) C12H10FN3O4 详情 详情
(XII) 64700   C12H10FN3O4 详情 详情
(XIII) 64698 5-ethenyl-2-{hydroxy[6-(methyloxy)-4-quinolinyl]methyl}-1-methyl-1-azoniabicyclo[2.2.2]octane hydroxide C21H28N2O3 详情 详情
(XIV) 64699   C33H38FN5O7 详情 详情
(XV) 16072 2',5'-Dioxo-3,4-dihydro-2H-spiro[1-benzopyran-4,4'-imidazolidin]-2-ylcarboxylic acid C12H10N2O5 详情 详情
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