CAS: 189028-93-1; (S)-1-(4-Fluorophenyl)-5-(2-Oxo-4-Phenyloxazolidin-3-yl)Pentane-1,5-Dione

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CAS号99395-88-7 (S)-(+)-4-苯基-2-噁唑烷酮 | CAS号149437-76-3 4-(4-氟苯甲酰基)丁酸 | CAS号3282-30-2 特戊酰氯 | CAS号186343-35-1 (S)-5-phenyl-1,... | CAS号1246853-48-4 (R,S)-3-[5-(4-f... | CAS号189028-95-3 (4S)-3-[(5S)-5-... | CAS号190595-65-4 依折麦布中间体

(R,S)-3-[5-(4-Fluorophenyl)-5-Hydroxy-Pentanoyl]-4-Phenyl-Oxazolidin-2-One置于4-二甲氨基吡啶,Candida Antarctica B Lipase,三乙胺,Pyridinium Chlorochromate,磷脂酶b体系中,用 Aq. Phosphate Buffer,二氯甲烷,异丙醚,甲苯 用作溶剂,化学反应 246.0H,反应生成(4S)-3-[5-(4-氟苯基)-1,5-二氧代戊基]-4-苯基-2-恶唑烷酮
参考文献:Lipase Catalyzed Kinetic Resolution For The Production Of (S)-3-[5-(4-Fluoro-Phenyl)-5-Hydroxy-Pentanoyl]-4-Phenyl-Oxazolidin-2-One: An Intermediate For The Synthesis Of Ezetimibe
标题:Lipase Catalyzed Kinetic Resolution For The Production Of (S)-3-[5-(4-Fluoro-Phenyl)-5-Hydroxy-Pentanoyl]-4-Phenyl-Oxazolidin-2-One: An Intermediate For The Synthesis Of Ezetimibe
摘要:Efficient Enzymatic Methods Were Developed For The Synthesis Of (S)-3-[5-(4-Fluoro-Phenyl)-5-Hydroxy-Pentanoyl]-4-Phenyl-Oxazolidin-2-One,By Transesterification Of (Rs)-3-[5-(4-Fluorophenyl)-5-Hydroxypentanoyl]-4(S)-4-Phenyl-1,3-Oxazolidin-2-One [(R,S)-Fop Alcohol] And Hydrolysis Of (Rs)-1-(4-Fluorophenyl)-5-Oxo-5-[(S)-2-Oxo-4-Phenyloxazolidin-3-Yl] Pentyl Acetate [(R,S)-Fop Acetate] Using Lipase As Enzyme Source. The Synthesized S-Diastereomer Is An Intermediate For The Potent Cholesterol Absorption Inhibitor,Ezetimibe. Among Various Lipases Tried,Candida Rugosa Lipase In Diisopropyl Ether Was Best For Both The Reactions. Vinyl Acetate Was Found As Suitable Acyl Donor In Transesterification Reaction. A Higher Amount Of Enzyme (500 Mg) Was Required For The Transesterification Of 10 Mm Substrate; It May Be Due To The Enzyme Denaturation By Acetaldehyde Formed In The Reaction. The Ester Hydrolysis Reaction Worked Well,Excellent Conversion And De Were Obtained At 40 Degrees C,Ph 7. The 300 Mg Enzyme Hydrolyzed 120 Mg (R,S)-Fop Acetate With 50% Conversion And 99.5% De. (C) 2012 Elsevier B.V. All Rights Reserved.
Doi:10.1016/j.Molcatb.2012.08.014

专利信息

专利号:US-2008032964-A1
优先权日:2006-04-10
标题:Process for the synthesis of azetidinone
发明人：KANSAL VINOD K; AHMAD SUHAIL; MARIAPPAN SHANMUGAVEL; TYAGI BHUPENDRA; PERLMAN NURIT; LE PAIH JACQUES; ZANOTTI-GEROSA ANTONIO
权利人:KANSAL VINOD K; AHMAD SUHAIL; MARIAPPAN SHANMUGAVEL; TYAGI BHUPENDRA; PERLMAN NURIT; LE PAIH JACQUES; ZANOTTI-GEROSA ANTONIO
摘要:Provided are intermediates useful for the synthesis of hydroxyl-alkyl substituted azetidinones, processes of their preparation, and processes for the synthesis of certain hydroxyl-alkyl substituted azetidinones. Also provided are processes for the synthesis of 1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone, or ezetimibe.

专利号:US-8383810-B2
优先权日:2004-12-20
标题:Process for the synthesis of azetidinones
发明人：THIRUVENGADAM TIRUVETTIPURAM K; CHIU JOHN S; FU XIAOYONG; MCALLISTER TIMOTHY L
权利人:MERCK SHARP & DOHME; THIRUVENGADAM TIRUVETTIPURAM K; CHIU JOHN S; FU XIAOYONG; MCALLISTER TIMOTHY L
摘要:A process is provided for preparing azetidinones useful as intermediates in the synthesis of penems and as hypocholesterolemic agents, comprising reacting a β-(substituted-amino)amide, a β-(substituted-amino)acid ester, or a β-(substituted-amino)thiolcarbonic acid ester with a silylating agent and a cyclizing agent selected from the group consisting of alkali metal carboxylates, quaternary ammonium carboxylates, quaternary ammonium hydroxides, quaternary ammonium alkoxides, quaternary ammonium aryloxides and hydrates thereof, or the reaction product of: (i) at least one quaternary ammonium halide and at least one alkali metal carboxylate; or (ii) at least one quaternary ammonium chloride, quaternary ammonium bromide, or quaternary ammonium iodide and at least one alkali metal fluoride, wherein a quaternary ammonium moiety of the cyclizing agent is unsubstituted or substituted by one to four groups independently selected from the group consisting of alkyl, arylalkyl and arylalkyl-alkyl.

专利号:US-6207822-B1
优先权日:1998-12-07
标 题:Process for the synthesis of azetidinones
发明人：THIRUVENGADAM TIRUVETTIPURAM K; FU XIAOYONG; TANN CHOU-HONG; MCALLISTER TIMOTHY L; CHIU JOHN S; COLON CESAR
权利人:SCHERING CORP
摘要:This invention provides a process for preparing the hypocholesterolemic compoundcomprising:(a) reacting p-fluorobenzoylbutyric acid with pivaloyl chloride and acylating the product with a chiral auxiliary to obtain a ketone of formula IV:(b) reducing the ketone of formula IV in the presence of a chiral catalyst to an alcohol:(c) reacting the chiral alcohol of step (b), an imine and a silyl protecting agent, then condensing the protected compounds to obtain a beta-(substituted-amino)amide of formula VII:(d) cyclizing the beta-(substituted-amino)amide of formula VII with a silylating agent and a fluoride ion catalyst to obtain a protected lactam of the formula VIII:and removing the protecting groups.The intermediates of formulas VII and VIII are also claimed.

专利号:US-2003204096-A1
优先权日:2002-03-25
标题 :Enantioselective synthesis of azetidinone intermediate compounds
发明人：FU XIAOYONG; MC ALLISTER TIMOTHY L; THIRUVENGADAM T K; TANN CHOU-HONG
权利人:SCHERING CORP
摘要:The application relates to a process for preparing a compound of Formula I n n n This compound is an intermediate used to produce compounds that are useful as hypocholesterolemic agents in the treatment and prevention of atheroschlerosis.

专利号:US-9040688-B2
优先权日:2009-03-31
标 题 :Intermediates in the preparation of 1,4-diphenyl azetidinone
发明人：SRIVASTAVA DHANANJAI; SHAKYA RAJIV KUMAR; CHAUDHARI NAMRATA ANIL; ANSARI INAMUS SAQLAIN; SINGH GIRIJ PAL
权利人:SRIVASTAVA DHANANJAI; SHAKYA RAJIV KUMAR; CHAUDHARI NAMRATA ANIL; ANSARI INAMUS SAQLAIN; SINGH GIRIJ PAL; LUPIN LTD
摘要:The process of the present invention relates to a method for the synthesis of a 1,4-diphenylazetidinone of formula (VIII) by using novel oxime intermediates.

专利号:US-6627757-B2
优先权日:2001-03-28
标题 :Enantioselective synthesis of azetidinone intermediate compounds
发明人：FU XIAOYONG; MCALLISTER TIMOTHY L; THIRUVENGADAM T K; TANN CHOU-HONG
权利人:SCHERING CORP
摘要:The application relates to a process for preparing a compound of Formula IThis compound is an intermediate used to produce compounds that are useful as hypocholesterolemic agents in the treatment and prevention of atheroschlerosis.