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【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%

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)

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
Extended Information