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【结 构 式】

【分子编号】33228

【品名】2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)acetic acid

【CA登记号】

【 分 子 式 】C5H6N2O2S

【 分 子 量 】158.18092

【元素组成】C 37.97% H 3.82% N 17.71% O 20.23% S 20.27%

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:(IX)

The condensation of 7-acetoacetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid (VII) with the mercaptane (VI) by means of NaHCO3 in hot water gives 7-beta-amino-3-[1-[2-(N,N-dimethylamino)ethyl]-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (VIII), which is then condensed with 2-aminothiazol-4-ylacetic acid (IX) by means of N-hydroxysuccinimide and dicyclohexylcarbodiimide in THF. The free amino group of (VIII) is acylated with Cl2 and diketene giving the 4-chloro-3-oxobutyramido derivative (X), which is finally cyclized with thiourea (B) by means of NaHCO3 in acetone.

1 Numata, M.; et al. (Takeda Chemical Industries, Ltd.); 7-Alpha-(2-aminothiazole)acetamidocephalosporins. DE 2461478; FR 2255077; GB 1491018; NL 7416609; US 4080498; US 4421912; US 4517361 .
2 Blancafort, P.; Serradell, M.N.; Castaner, J.; Roberts, P.J.; Cefotiam. Drugs Fut 1979, 4, 6, 400.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(VI) 33224 1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetraazole-5-thiol; 1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetraazol-5-ylhydrosulfide 61607-68-9 C5H11N5S 详情 详情
(VII) 33225 (6R,7R)-7-(acetoacetamido)-3-[(acetoxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C14H16N2O7S 详情 详情
(VIII) 33226 (6R,7R)-7-amino-3-[([1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetraazol-5-yl]sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C13H19N7O3S2 详情 详情
(IX) 33228 2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)acetic acid C5H6N2O2S 详情 详情
(X) 33227 (6R,7R)-7-[(4-chloro-3-oxobutanoyl)amino]-3-[([1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetraazol-5-yl]sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C17H22ClN7O5S2 详情 详情
Extended Information