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【结 构 式】

【分子编号】44602

【品名】thiourea

【CA登记号】

【 分 子 式 】CH4N2S

【 分 子 量 】76.12224

【元素组成】C 15.78% H 5.3% N 36.8% S 42.12%

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:(I)

The synthesis of [14C]-labeled cefepime has been reported: The cyclization of [14C]-thiourea (I) with 4-bromo-2-(methoxyimino)-3-oxobutyric acid ethyl ester (II) in ethanol gives 2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetic acid ethyl ester (III), which is hydrolyzed with NaOH in methanol to the corresponding free acid (IV). The esterification of (IV) with 1-hydroxybenzotriazole (V) by means of dicyclohexylcarbodiimide in THF affords the corresponding active ester (VI), which is condensed with 7-amino-3-(1-methylpyrrolidiniomethyl)-3-cephem-4-carboxylate (VII) by means of NaOH in THF-water and isolated as the sulfate salt (VIII). Finally, this compound is treated with triethylamine in N-methyl-2-pyrrolidone.

1 Swigor, J.E.; Standridge, R.T.; Synthesis of 7-[alpha-(2-amino-[2-14C]thiazol-4-yl)-alpha-(Z)-methoxyiminoacetamido]-3-(1-methylpyrrolidinio)methyl-3-cephem-4-carboxylate hydrochloride ([14C]cefepime hydrochloride). J Label Compd Radiopharm 1993, 33, 8, 759.
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) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(I) 44602 thiourea CH4N2S 详情 详情
(II) 10181 ethyl 4-bromo-2-(methoxyimino)-3-oxobutanoate 60845-87-6 C7H10BrNO4 详情 详情
(III) 10182 Ethyl 2-(2-aminothiazole-4-yl)-2-methoxyiminoacetate; ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetate; 2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetic acid ethyl ester 64485-88-7 C8H11N3O3S 详情 详情
(III) 44603 ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetate C8H11N3O3S 详情 详情
(IV) 10183 (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetic acid;2-(2-Amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetic acid 66338-96-3 C5H5N3O3S 详情 详情
(IV) 44604 2-(2-amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetic acid C5H5N3O3S 详情 详情
(V) 10184 1H-1,2,3-Benzotriazol-1-ol; 1-Hydroxybenzotriazole; 1H-Benzotriazol-1-ol; 1-Benzotriazolol 2592-95-2 C6H5N3O 详情 详情
(VI) 10185 1-(2-Amino-1,3-thiazol-4-yl)-2-(1H-1,2,3-benzotriazol-1-yloxy)-2-oxo-1-ethanone oxime C11H8N6O3S 详情 详情
(VI) 44605 1-(2-amino-1,3-thiazol-4-yl)-2-(1H-1,2,3-benzotriazol-1-yloxy)-2-oxo-1-ethanone oxime C11H8N6O3S 详情 详情
(VII) 10186 (6R,7R)-7-amino-3-[(1-methyltetrahydro-1H-pyrrolium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C13H19N3O3S 详情 详情
(VIII) 10187 1-[((6R,7R)-7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]-1-methyltetrahydro-1H-pyrrolium C19H25N6O5S2 详情 详情
(VIII) 44606 1-[((6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]-1-methylpyrrolidinium C19H25N6O5S2 详情 详情
Extended Information