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【结 构 式】

【分子编号】15752

【品名】2-[5-[(tert-butoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-(methoxyimino)acetic acid

【CA登记号】

【 分 子 式 】C10H14N4O5S

【 分 子 量 】302.31112

【元素组成】C 39.73% H 4.67% N 18.53% O 26.46% S 10.61%

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:(V)

This compound can be prepared by two related ways: 1) The condensation of (6R,7R)-7-amino-3-(3-oxobutyryloxy)-3-cephem-4-carboxylic acid (I) with 2-[5-(tert-butoxycarbonylamino)-1,2,4-thiadiazol-3-yl]-2(Z)-(methoxyimino)acetic acid (II), by means of PCl5 and bis(trimethylsilyl)acetamide (BSA) gives the corresponding amide (III), which is thencondensed with imidazo[1,2-b]pyridazine (IV) by means of KI in hot aqueous acetonitrile. 2) The condensation of 2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]-2(Z)-(methoxyimino)acetic acid (V) with cephem compound (I) by means of PCl5 and triethylamine yields the corresponding amide (VI), which is deprotected with trifluoroacetic acid to afford free amide (III), already obtained.

1 Miyake, A.; Kondo, M.; Fujino, M. (Takeda Chemical Industries, Ltd.); Antibacterial cpds., their production and use. AU 8541700; AU 8654168; EP 0160252; EP 0203271; ES 8606363; ES 8705892; ES 8706692; ES 8707245; JP 1985231684; JP 1987149682; WO 8504879; WO 8505620; WO 8605183; WO 8605184 .
2 Prous, J.; Castaner, J.; Cefozopran Hydrochloride. Drugs Fut 1992, 17, 9, 771.
3 Yoshimura, Y.; Hashimoto, N.; Miyake,A.; Nishimura, T.; Yamaoka, M.; Imada, A.; Studies on condensed-heterocyclic azolium cephalosporins. IV. Synthesis and antibacterial activity of 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-alkoxyiminoacetamido]-3-(condensed-heterocyclic azolium)methyl cephalosporins including SCE-2787. J Antibiot 1992, 45, 5, 709-20.
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) 15748 (6R,7R)-3-[(acetoacetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C12H14N2O6S 详情 详情
(II) 11757 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid C5H6N4O3S 详情 详情
(III) 15750 (6R,7R)-3-[(acetoacetoxy)methyl]-7-[[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C17H18N6O8S2 详情 详情
(IV) 15751 imidazo[1,2-b]pyridazine C6H5N3 详情 详情
(V) 15752 2-[5-[(tert-butoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-(methoxyimino)acetic acid C10H14N4O5S 详情 详情
(VI) 15753 (6R,7R)-3-[(acetoacetoxy)methyl]-7-[[2-[5-[(tert-butoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C22H26N6O10S2 详情 详情
Extended Information