【结 构 式】 |
【分子编号】37414 【品名】(6R,7R)-7-amino-3-[[(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 【CA登记号】 |
【 分 子 式 】C12H13N5O5S2 【 分 子 量 】371.39792 【元素组成】C 38.81% H 3.53% N 18.86% O 21.54% S 17.27% |
合成路线1
该中间体在本合成路线中的序号:(VII)The reaction of methylhydrazin (I) with potassium thiocyanate (II) gives N-methyl-N-aminothiourea (III), which is cyclized with dimethyl oxalate (IV) by means of sodium methoxide in methanol to afford 2,5-dihydro-6-hydroxy-2-methyl-3-mercapto-5-oxo-1,2,4-triazine (V). The reaction of (V) with 7-aminocephalosporanic acid (VI) in a buffer solution at pH 6.5 gives 7-amino-3,4-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (VII), which is condensed with 2-(2-chloroacetamido-4-thiazolyl)-2-[(Z)-methoxyimino]acetyl chloride (VIII) at pH 2 yielding 7-]2-(2-chloroacetamido-4-thiazolyl)-2-[(Z)-methoxyimino]acetamido-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (IX). Finally, this compound is hydrolyzed and treated with sodium hydroxide.
【1】 Neuman, M.; Cefatriaxon. Drugs Fut 1981, 6, 3, 132. |
【2】 Reiner, R.; et al.; Ro-13-9904/001, a novel potent and long-acting parenteral cephalosporin. J Antibiot 1980, 32, 7, 783-786. |
【3】 Reiner, R.; Montavon, M. (F. Hoffmann-La Roche AG); Cephalosporin derivs. and process for their preparation. DE 2922036 . |
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) | 12091 | 1-Methylhydrazine; Monomethyl hydrazine | 60-34-4 | CH6N2 | 详情 | 详情 |
(II) | 37410 | Potassium thiocyanate | 333-20-0 | CKNS | 详情 | 详情 |
(III) | 37411 | 1-methyl-1-hydrazinecarbothioamide | C2H7N3S | 详情 | 详情 | |
(IV) | 37412 | methyl 2-methoxy-2-oxoacetate;dimethyl oxalate;Methyl oxalate | 553-90-2 | C4H6O4 | 详情 | 详情 |
(V) | 37413 | 6-hydroxy-2-methyl-3-sulfanyl-1,2,4-triazin-5(2H)-one | C4H5N3O2S | 详情 | 详情 | |
(VI) | 22747 | (6R,7R)-3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C10H12N2O5S | 详情 | 详情 | |
(VII) | 37414 | (6R,7R)-7-amino-3-[[(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C12H13N5O5S2 | 详情 | 详情 | |
(VIII) | 32659 | 2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-(methoxyimino)acetyl chloride | 75532-64-8 | C8H7Cl2N3O3S | 详情 | 详情 |
(IX) | 37415 | (6R,7R)-7-[[2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-(methoxyimino)acetyl]amino]-3-[[(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C20H19ClN8O8S3 | 详情 | 详情 |