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【结 构 式】

【分子编号】20339

【品名】(7R)-7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

【CA登记号】30246-33-4

【 分 子 式 】C11H12N4O3S3

【 分 子 量 】344.43944

【元素组成】C 38.36% H 3.51% N 16.27% O 13.94% S 27.93%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VI)

2) The reaction of 7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (VI) with 2-O-(tert-butoxycarbonyl-L-alanyl)mandelic acid (VII) by means of triethylamine in THF gives the corresponding amide (VIII), which is then esterified with dioxolone (II) as before to afford the protected product (V), already obtained.

1 Prous, J.; Castaner, J.; CEFCANEL DALOXATE HYDROCHLORIDE < Prop INNM >. Drugs Fut 1989, 14, 1, 13.
2 Kakeya, N.; Nishizawa, S.; Nishimura, K.; Yoshimi, A.; Tamaki, S.; Mori, T.; Kitao, K.; KY-109, A new bifunctional pro-drug of a cephalosporin. Chemistry, physico-chemical and biological properties. J Antibiot 1985, 38, 3, 380-9.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 20338 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (7R)-7-[[(2R)-2-([2-[(tert-butoxycarbonyl)amino]propanoyl]oxy)-2-phenylethanoyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C32H35N5O11S3 详情 详情
(VI) 20339 (7R)-7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 30246-33-4 C11H12N4O3S3 详情 详情
(VII) 20340 (11R)-2,2,8-trimethyl-4,6,9-trioxo-11-phenyl-3,5,10-trioxa-7-azadodecan-12-oic acid C17H21NO8 详情 详情
(VIII) 20341 (7R)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-7-[[(2R)-5,11,11-trimethyl-4,7,9-trioxo-2-phenyl-3,8,10-trioxa-6-azadodec-1-anoyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C28H31N5O10S3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

3) The reaction of the 7-aminocephem derivative (VI) with ethyl acetoacetate (IX) at room temperature gives the 3-aminocrotonate derivative (X), which is esterified with dioxolone (II) as before yielding the ester derivative (XI). The acidic (HCl) hydrolysis of (XI) in methanol-dichloromethane affords the 7-aminocephem derivative (XII) , which is finally condensed with 2-O-(tert-butoxycarbonyl-L-alanyl)mandelic acid (VII) by means of dicyclohexylcarbodiimide (DCC) in dichloromethane to yield the protected product (V), already obtained.

1 Nishizawa, S.; et al. (Kyoto Pharmaceutical Industries, Ltd.); Production of cephalosporin compounds.. JP 85034975 .
2 Nishizawa, S.; Tamaki, S.; Kakeya, N.; Kitao, K. (Kyoto Pharmaceutical Industries, Ltd.); Cephalosporin cpds.. WO 8505360 .
3 Prous, J.; Castaner, J.; CEFCANEL DALOXATE HYDROCHLORIDE < Prop INNM >. Drugs Fut 1989, 14, 1, 13.
4 Kakeya, N.; Nishizawa, S.; Nishimura, K.; Yoshimi, A.; Tamaki, S.; Mori, T.; Kitao, K.; KY-109, A new bifunctional pro-drug of a cephalosporin. Chemistry, physico-chemical and biological properties. J Antibiot 1985, 38, 3, 380-9.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 20338 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (7R)-7-[[(2R)-2-([2-[(tert-butoxycarbonyl)amino]propanoyl]oxy)-2-phenylethanoyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C32H35N5O11S3 详情 详情
(VI) 20340 (11R)-2,2,8-trimethyl-4,6,9-trioxo-11-phenyl-3,5,10-trioxa-7-azadodecan-12-oic acid C17H21NO8 详情 详情
(VII) 20339 (7R)-7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 30246-33-4 C11H12N4O3S3 详情 详情
(IX) 11819 ethyl acetoacetate; ethyl 3-oxobutanoate;Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate 141-97-9 C6H10O3 详情 详情
(X) 20343 (7R)-7-[[(Z)-4-ethoxy-1-methyl-3,4-dioxo-1-butenyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C18H20N4O6S3 详情 详情
(XI) 20344 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (7R)-7-[[(Z)-4-ethoxy-1-methyl-3,4-dioxo-1-butenyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C23H24N4O9S3 详情 详情
(XII) 20345 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (7R)-7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C16H16N4O6S3 详情 详情
Extended Information