methyl 2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]acetate -Drug Synthesis Database

【结构式】

【分子编号】45479

【品名】methyl 2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]acetate

【CA登记号】

【分子式】C₇H₉N₃O₄S

【分子量】231.23228

【元素组成】C 36.36% H 3.92% N 18.17% O 27.68% S 13.87%

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：(III)

Thiadiazole (II) was synthesized from 3-aminoisoxazole (I) following a known procedure. Esterification of (II) to give (III) was carried out by treatment with MeOH and SOCl2. Subsequent oxidation of (III) employing I2 in DMSO provided keto ester (IV), which was converted into oxime (V) and then protected as the O-trityl derivative (VI). Basic hydrolysis of the methyl ester group yielded carboxylic acid (VII). Then, coupling of acid (VII) with aminocephalosporin (VIII) by means of POCl3 furnished the corresponding amide (IX).

参考文献中间体

合成目标

【1】 Griffith, D.; Blais, J.; Hevker, S.; Price, M.; Huie, K.; Halas, S.; Cho, A.; Dudley, M.; Lee, V.; Ludwikow, M.; Chen, S.; Chemberland, S.; Glinka, T.; Discovery of novel anti-MRSA cephalosporin RWJ-333441 (MC-04,546). Relationships between structure, antibacterial activity, serum stability, pharmacokinetics and efficacy in a series of (3-heteroarylthio)cephems. 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1071.

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)	45477	3-isoxazolylamine; 3-isoxazolamine	1750-42-1	C₃H₄N₂O	详情	详情
(II)	45478	2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]acetic acid		C₆H₇N₃O₄S	详情	详情
(III)	45479	methyl 2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]acetate		C₇H₉N₃O₄S	详情	详情
(IV)	45480	methyl 2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-oxoacetate		C₇H₇N₃O₅S	详情	详情
(V)	45481	methyl 2-(hydroxyimino)-2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]acetate		C₇H₈N₄O₅S	详情	详情
(VI)	45482	methyl 2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-[(trityloxy)imino]acetate		C₂₆H₂₂N₄O₅S	详情	详情
(VII)	45483	2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-[(trityloxy)imino]acetic acid		C₂₅H₂₀N₄O₅S	详情	详情
(VIII)	45484	benzhydryl (6R,7R)-7-amino-3-[(methylsulfonyl)oxy]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₂₁H₂₀N₂O₆S₂	详情	详情
(IX)	45485	benzhydryl (6R,7R)-7-([2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-[(trityloxy)imino]acetyl]amino)-3-[(methylsulfonyl)oxy]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₄₆H₃₈N₆O₁₀S₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

参考文献中间体

合成目标

【1】 Griffith, D.; Blais, J.; Hevker, S.; Price, M.; Huie, K.; Halas, S.; Cho, A.; Dudley, M.; Lee, V.; Ludwikow, M.; Chen, S.; Chemberland, S.; Glinka, T.; Discovery of novel anti-MRSA cephalosporin RWJ-333441 (MC-04,546). Relationships between structure, antibacterial activity, serum stability, pharmacokinetics and efficacy in a series of (3-heteroarylthio)cephems. 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1071.

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)	45477	3-isoxazolylamine; 3-isoxazolamine	1750-42-1	C₃H₄N₂O	详情	详情
(II)	45478	2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]acetic acid		C₆H₇N₃O₄S	详情	详情
(III)	45479	methyl 2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]acetate		C₇H₉N₃O₄S	详情	详情
(IV)	45480	methyl 2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-oxoacetate		C₇H₇N₃O₅S	详情	详情
(V)	45481	methyl 2-(hydroxyimino)-2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]acetate		C₇H₈N₄O₅S	详情	详情
(VI)	45482	methyl 2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-[(trityloxy)imino]acetate		C₂₆H₂₂N₄O₅S	详情	详情
(VII)	45483	2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-[(trityloxy)imino]acetic acid		C₂₅H₂₀N₄O₅S	详情	详情
(VIII)	45484	benzhydryl (6R,7R)-7-amino-3-[(methylsulfonyl)oxy]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₂₁H₂₀N₂O₆S₂	详情	详情
(IX)	45485	benzhydryl (6R,7R)-7-([2-[5-[(methoxycarbonyl)amino]-1,2,4-thiadiazol-3-yl]-2-[(trityloxy)imino]acetyl]amino)-3-[(methylsulfonyl)oxy]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₄₆H₃₈N₆O₁₀S₃	详情	详情

Extended Information