(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (7R)-7-[[(2R)-2-hydroxy-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 -Drug Synthesis Database

【结构式】

【分子编号】20336

【品名】(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (7R)-7-[[(2R)-2-hydroxy-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

【CA登记号】

【分子式】C₂₄H₂₂N₄O₈S₃

【分子量】590.65884

【元素组成】C 48.8% H 3.75% N 9.49% O 21.67% S 16.29%

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：(III)

1) The esterification of 7-[(R)-mandelamido]-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (KY-087; I) with 4-bromomethyl-5-methyl-1,3-dioxol-2-one (II) by means of potassium acetate in DMF gives the corresponding ester (KY-106; III), which is condensed with tert-butoxycarbonyl-L-alanine (IV) by means of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMP) in dichloromethane affording the protected final product (V). Finally, this compound is deprotected with HCl in methanol-acetone.

参考文献中间体

合成目标

【1】 Kaneya, N.; Nishizawa, S.; Tamaki, S.; Kitao, K. (Kyoto Pharmaceutical Industries, Ltd.); Antibiotic amino acid derivatives of cephalosporins.. JP 59116292; US 4605651; WO 8401949 .
【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.
【3】 Prous, J.; Castaner, J.; CEFCANEL DALOXATE HYDROCHLORIDE < Prop INNM >. Drugs Fut 1989, 14, 1, 13.

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)	20334	(7R)-7-[[2-(2-hydroxyphenyl)acetyl]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		C₁₉H₁₈N₄O₅S₃	详情	详情
(II)	13462	4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one	80715-22-6	C₅H₅BrO₃	详情	详情
(III)	20336	(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (7R)-7-[[(2R)-2-hydroxy-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		C₂₄H₂₂N₄O₈S₃	详情	详情
(IV)	20337	N-(tert-butoxycarbonyl)alanine		C₈H₁₅NO₄	详情	详情
(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

Extended Information