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【结 构 式】 
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【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% |
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 |