methyl (2S)-3-phenyl-2-([[(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)amino]carbonyl]amino)propanoate -Drug Synthesis Database

【结构式】

【分子编号】38889

【品名】methyl (2S)-3-phenyl-2-([[(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)amino]carbonyl]amino)propanoate

【CA登记号】

【分子式】C₁₃H₁₄N₄O₃S₂

【分子量】338.41132

【元素组成】C 46.14% H 4.17% N 16.56% O 14.18% S 18.95%

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)

The reaction of L-phenylalanine methyl ester (I) with phosgene and pyridine in dichloromethane gives the isocyanate (II) (1), which is condensed with 5-amino-1,3,4-thiadiazol-2(3H)-thione (III) in THF to yield the urea (IV). Finally, this compound is treated with methylamine in ethanol to affords the target compound.

参考文献中间体

合成目标

【1】 Mitchell, M.A.; Hendges, S.K.; Jacobsen, E.J.; et al.; Synthesis of a series of stromelysin-selective thiadiazole urea matrix metalloproteinase inhibitors. J Med Chem 1999, 42, 9, 1525.
【2】 Jacobsen, E.J.; Mitchell, M.A.; Schostarez, H.J.; Harper, D.E. (Pharmacia & Upjohn AB); Thiadiazolyl(thio)ureas useful as matrix metalloprotease inhibitors. EP 0900211; JP 2000509039; WO 9740031 .
【3】 Mitchell, M.A.; Schostarez, H.J.; Harper, D.E.; Jacobsen, E.J. (Pharmacia Corp.); Thiadiazole derivs. useful for the treatment of diseases related to connective tissue degradation. US 5847148 .

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)	12324	methyl (2R)-2-amino-3-phenylpropanoate	21685-51-8	C₁₀H₁₃NO₂	详情	详情
(II)	38888	methyl (2S)-2-isocyanato-3-phenylpropanoate	40203-94-9	C₁₁H₁₁NO₃	详情	详情
(III)	24397	5-amino-1,3,4-thiadiazole-2(3H)-thione	2349-67-9	C₂H₃N₃S₂	详情	详情
(IV)	38889	methyl (2S)-3-phenyl-2-([[(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)amino]carbonyl]amino)propanoate		C₁₃H₁₄N₄O₃S₂	详情	详情

Extended Information