(Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetic acid；2-(2-Amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetic acid -Drug Synthesis Database

【结构式】

【分子编号】10183

【品名】(Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetic acid；2-(2-Amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetic acid

【CA登记号】66338-96-3

【分子式】C₅H₅N₃O₃S

【分子量】187.17912

【元素组成】C 32.08% H 2.69% N 22.45% O 25.64% S 17.13%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

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.

参考文献中间体

合成目标

【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

合成路线2

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

【1】 Cabri W,Alpegiani M,Pozzi G,et al.A process for the preparation of cephalosporins side chain:WO,Patent 2.003,040,116,2003.

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)	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
(II)	69623	triethylamine (Z)-2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)acetate		C₂₄H₁₉N₃O₃S.C₆H₁₅N	详情	详情
(III)	69619	(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)ethanethioate		C₃₁H₂₂N₄O₂S₃	详情	详情

Extended Information