2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl chloride -Drug Synthesis Database

【结构式】

【分子编号】45073

【品名】2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl chloride

【CA登记号】

【分子式】C₅H₅ClN₄O₂S

【分子量】220.63916

【元素组成】C 27.22% H 2.28% Cl 16.07% N 25.39% O 14.5% S 14.53%

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：(IV)

A new synthesis for [14C]-E-1040 has been described: The cyclization of [14C]-labeled potassium thiocyanate (I) with 2-(N-chlorocarboxamidino)-2-(methoxyimino)acetic acid (II) in methanol by means of triethylamine gives 2-(2-aminothiazol-4-yl)-2(Z)-(methoxyimino)acetic acid (III), which is treated with PCl5 in dichloromethane, yielding the corresponding acyl chloride (IV). Finally, this compound is condensed with 7-amino-3-(4-carbamoylquinuclidinio-1-ylmethyl)-3-cephem-4-carboxylate (V) by means of sodium acetate in dichloromethane.

参考文献中间体

合成目标

【1】 Sugiyama, I.; Nomoto, S.; Mizuo, H.; Yamauchi, H.; Synthesis of (6R,7R)-7-[2-(5-amino-1,2,4-[5-C-14]thiadiazol-3-yl)-(Z)-2-methoxyiminoacetamido]-3-[(4-carbomoyl-1-quinuclidinio)methyl]ceph-3-em-4-carboxylate([C-14]E1040). J Label Compd Radiopharm 1991, 29, 12, 1309.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(II)	11756	3-Amino-3-(chloroimino)-2-(methoxyimino)propionic acid	C₄H₆ClN₃O₃	详情	详情
(III)	11757	2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid	C₅H₆N₄O₃S	详情	详情
(III)	45072	2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid	C₅H₆N₄O₃S	详情	详情
(IV)	11758	2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl chloride	C₅H₅ClN₄O₂S	详情	详情
(IV)	45073	2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl chloride	C₅H₅ClN₄O₂S	详情	详情
(V)	11759	(6R,7R)-7-amino-3-[[4-(aminocarbonyl)-1-azoniabicyclo[2.2.2]oct-1-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₁₆H₂₂N₄O₄S	详情	详情

Extended Information