methyl (2S)-2-amino-3-[3,4-bis(acetyloxy)phenyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】61955

【品名】methyl (2S)-2-amino-3-[3,4-bis(acetyloxy)phenyl]propanoate

【CA登记号】

【分子式】C₁₄H₁₇NO₆

【分子量】295.29212

【元素组成】C 56.94% H 5.8% N 4.74% O 32.51%

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)

Esterification of L-Dopa (I) with thionyl chloride in methanol leads to the methyl ester (II). The phenolic hydroxyls of (II) are further acylated by acetyl chloride in trifluoroacetic acid to produce diacetate (III). Treatment of the protected derivative of L-Dopa (III) with diphosgene gives rise to isocyanate (IV). This is then coupled to entacapone (V) in refluxing acetonitrile to furnish carbamate (VI). The acetate ester groups of (VI) are finally removed by treatment with 3N HCl in acetone.

参考文献中间体

合成目标

【1】 Leppanen, J.; et al.; Design and synthesis of a novel L-dopa-entacapone codrug. J Med Chem 2002, 45, 6, 1379.

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)	15272	(2S)-2-amino-3-(3,4-dihydroxyphenyl)propionic acid; 3-hydroxy-L-tyrosine; Levodopa	59-92-7	C₉H₁₁NO₄	详情	详情
(II)	29568	methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate		C₁₀H₁₃NO₄	详情	详情
(III)	61955	methyl (2S)-2-amino-3-[3,4-bis(acetyloxy)phenyl]propanoate		C₁₄H₁₇NO₆	详情	详情
(IV)	61956	methyl (2S)-3-[3,4-bis(acetyloxy)phenyl]-2-isocyanatopropanoate		C₁₅H₁₅NO₇	详情	详情
(V)	61957	(E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide		C₁₄H₁₅N₃O₅	详情	详情
(VI)	61958	methyl (2S)-3-[3,4-bis(acetyloxy)phenyl]-2-[({5-[(E)-2-cyano-3-(diethylamino)-3-oxo-1-propenyl]-2-hydroxy-3-nitrophenoxy}carbonyl)amino]propanoate		C₂₉H₃₀N₄O₁₂	详情	详情

Extended Information