有机化学
有機化學
유궤화학
CHINESE JOURNAL OF ORGANIC CHEMISTRY
2009年
12期
1997-1999
,共3页
吕世翔%郭阳辉%王亚平%王相晶%向文胜
呂世翔%郭暘輝%王亞平%王相晶%嚮文勝
려세상%곽양휘%왕아평%왕상정%향문성
(R)-4-氰基-3-羟基丁酸乙酯%L-(一)-苹果酸%(3S)-3,4-二羟基丁酸乙酯%(S)-4-溴-3-羟基丁酸乙酯%合成
(R)-4-氰基-3-羥基丁痠乙酯%L-(一)-蘋果痠%(3S)-3,4-二羥基丁痠乙酯%(S)-4-溴-3-羥基丁痠乙酯%閤成
(R)-4-청기-3-간기정산을지%L-(일)-평과산%(3S)-3,4-이간기정산을지%(S)-4-추-3-간기정산을지%합성
(R)-4-cyano-3-hydroxybutyric acid ethyl ester%L-(-)-malic acid%(3S)-3,4-dihydroxybutyric acid ethyl ester%(S)-4-bromo-3-hydroxybutyric acid ester%synthesis
研究了一条新的路线用于他汀类药物的重要中间体(R)-4-氰基-3-羟基丁酸乙酯的合成.以廉价、易得的L-(一)-苹果酸为起始原料,经酯化、还原、溴代和氰化四步反应得到目标化合物(R).4-氰基-3-羟基丁酸乙酯,合成总收率为56.7%.所有中间体和最终产物均由ESI-MS,~H NMR和~(13)C NMR光谱及比旋光度表征并与文献值比较.该方法原料易得、操作简便、收率良好,产物容易分离纯化,是一条适合大规模制备(R)-4-氰基-3-羟基丁酸乙酯的新合成工艺路线.
研究瞭一條新的路線用于他汀類藥物的重要中間體(R)-4-氰基-3-羥基丁痠乙酯的閤成.以廉價、易得的L-(一)-蘋果痠為起始原料,經酯化、還原、溴代和氰化四步反應得到目標化閤物(R).4-氰基-3-羥基丁痠乙酯,閤成總收率為56.7%.所有中間體和最終產物均由ESI-MS,~H NMR和~(13)C NMR光譜及比鏇光度錶徵併與文獻值比較.該方法原料易得、操作簡便、收率良好,產物容易分離純化,是一條適閤大規模製備(R)-4-氰基-3-羥基丁痠乙酯的新閤成工藝路線.
연구료일조신적로선용우타정류약물적중요중간체(R)-4-청기-3-간기정산을지적합성.이렴개、역득적L-(일)-평과산위기시원료,경지화、환원、추대화청화사보반응득도목표화합물(R).4-청기-3-간기정산을지,합성총수솔위56.7%.소유중간체화최종산물균유ESI-MS,~H NMR화~(13)C NMR광보급비선광도표정병여문헌치비교.해방법원료역득、조작간편、수솔량호,산물용역분리순화,시일조괄합대규모제비(R)-4-청기-3-간기정산을지적신합성공예로선.
A novel method for synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester (1), a key intermediate of statins, was reported. The target compound 1 was successfully prepared via esterification, reduction, bromization and cyanation processes by using L-(-)-malic acid (2), which is an inexpensive and easily available starting material. The overall yield was 56.7%. The structures of intermediates and final product were determined by ESI-MS, ~1H NMR, ~(13)C NMR techniques, optical rotation and comparison with reported data. This method with the advantages of simply available starting material, easily conducted procedure, relatively high yield and easy purification is more suitable for scale-up production.
