methyl (2S)-2-([[(4S)-3-acetyl-1,3-thiazolidin-4-yl]carbonyl]amino)-3-[4-[(2,6-dichlorobenzyl)oxy]phenyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】40794

【品名】methyl (2S)-2-([[(4S)-3-acetyl-1,3-thiazolidin-4-yl]carbonyl]amino)-3-[4-[(2,6-dichlorobenzyl)oxy]phenyl]propanoate

【CA登记号】

【分子式】C₂₃H₂₄Cl₂N₂O₅S

【分子量】511.42544

【元素组成】C 54.02% H 4.73% Cl 13.86% N 5.48% O 15.64% S 6.27%

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：(V)

Coupling of N-acetyl-D-thioproline (I) with tyrosine methyl ester (II) using EDC and HOBt yielded dipeptide (III). Subsequent alkylation of the tyrosine phenolic group of (III) with 2,6-dichlorobenzyl bromide (IV) and NaH produced the dichlorobenzyl ether (V). The methyl ester group of (V) was finally hydrolyzed employing LiOH in aqueous THF.

参考文献中间体

合成目标

【1】 Head, J.C.; Warrellow, G.J.; Archibald, S.C. (Celltech Chiroscience plc); Anti-inflammatory tyrosine derivs.. EP 0984981; US 6093696; WO 9854207 .

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)	40791	(4S)-3-acetyl-1,3-thiazolidine-4-carboxylic acid	24877-72-3	C₆H₉NO₃S	详情	详情
(II)	21431	methyl (2S)-2-amino-3-(4-hydroxyphenyl)propanoate	1080-06-4	C₁₀H₁₃NO₃	详情	详情
(III)	40792	methyl (2S)-2-([[(4S)-3-acetyl-1,3-thiazolidin-4-yl]carbonyl]amino)-3-(4-hydroxyphenyl)propanoate		C₁₆H₂₀N₂O₅S	详情	详情
(IV)	40793	2-(bromomethyl)-1,3-dichlorobenzene	20443-98-5	C₇H₅BrCl₂	详情	详情
(V)	40794	methyl (2S)-2-([[(4S)-3-acetyl-1,3-thiazolidin-4-yl]carbonyl]amino)-3-[4-[(2,6-dichlorobenzyl)oxy]phenyl]propanoate		C₂₃H₂₄Cl₂N₂O₅S	详情	详情

Extended Information