KR840008022A - Method for preparing chiral aldehyde - Google Patents

Method for preparing chiral aldehyde Download PDF

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KR840008022A
KR840008022A KR1019840000917A KR840000917A KR840008022A KR 840008022 A KR840008022 A KR 840008022A KR 1019840000917 A KR1019840000917 A KR 1019840000917A KR 840000917 A KR840000917 A KR 840000917A KR 840008022 A KR840008022 A KR 840008022A
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South Korea
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general formula
lower alkyl
aldehyde
group
formula
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KR1019840000917A
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Korean (ko)
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허브쉬웨르랑 크리스티앙
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예안-야퀘스 오가이, 마인라트 쉬미트
에프. 호프만-라로슈 앤드 캄퍼니 아크티엔게젤샤프트
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Publication of KR840008022A publication Critical patent/KR840008022A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

내용 없음.No content.

Description

키랄 알데히드의 제조방법Method for preparing chiral aldehyde

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (11)

다음 일반식(Ⅱ)의 락톤을 알카리금속 메타과요도산염과 반응시킴을 특징으로 하여 다음 일반식(I)의 키랄 알데히드를 제조하는 방법.A process for preparing chiral aldehyde of the following general formula (I), characterized by reacting lactone of the following general formula (II) with an alkali metal metaperiodate. 상기식에서, R3및 R4는 각각 독립적으로 수소 또는 저급알킬을 나타내거나, 함께 저급 알킬렌을 나타낸다.Wherein R 3 and R 4 each independently represent hydrogen or lower alkyl, or together represent lower alkylene. 제1항에 따라 수득한 일반식(I)의 알데히드를 다음 일반식(Ⅳ)의 아민과 반응시키고 수득한 다음 일반식(Ⅴ)의 화합물을 염기의 존재하에, 다음 일반식(Ⅵ)의 카복실산의 반응성 유도체와 반응시킴을 특징으로 하여 다음 일반식(Ⅲ)의 키랄 β-락탐을 제조하는 방법.The aldehyde of general formula (I) obtained according to claim 1 is reacted with an amine of general formula (IV) and obtained, and then the compound of general formula (V) is present in the presence of a base, and the carboxylic acid of general formula (VI) A method for preparing chiral β-lactam of the following general formula (III), characterized by reacting with a reactive derivative of (III). 상기식에서, R1은 쉽게 분해될 수 있는 보호그룹을 나타내고, R2는 벤질옥시카보닐아미노, 아지도, 프탈이미도 또는 R5R6C=CR7-NH-그룹[여기에서, R5는 저급 알카노일, 저급 알콕시카보닐 또는 벤조일을 나타내고, R6는 수소, 저급알킬, 저급 알카노일, 저급 알콕시 카보닐 또는 시아노를 나타내고, R7은 수소 또는 저급 알킬을 나타낸다]을 나타내고, R3및 R4는 각각독립적으로 수소 또는 저급 알킬을 나타내거나, 함께 저급 알킬렌을 나타낸다.Wherein R 1 represents a protecting group that can be readily decomposed and R 2 represents benzyloxycarbonylamino, azido, phthalimido or R 5 R 6 C═CR 7 -NH-group [where R 5 Represents lower alkanoyl, lower alkoxycarbonyl or benzoyl, R 6 represents hydrogen, lower alkyl, lower alkanoyl, lower alkoxy carbonyl or cyano, and R 7 represents hydrogen or lower alkyl. 3 and R 4 each independently represent hydrogen or lower alkyl, or together represent lower alkylene. 제2항에 있어서, R2가 아지도, 프탈이미도 또는 ROCO-CH=C(CH3)-NH-그룹 [여기에서, R은 저급알킬을 나타낸다]을 나타내는 일반식 (Ⅵ)의 카복실산의 반응성 유도체가 사용되는 방법.The carboxylic acid of formula (VI) according to claim 2, wherein R 2 represents azido, phthalimido or ROCO—CH═C (CH 3 ) —NH—group wherein R represents lower alkyl. The method in which the reactive derivative is used. 제1항 내지 3항중 어느 하나에 있어서, 5,6-이소프로필리덴-L-쿨로노락톤을 일반식 (Ⅱ)의 출발물질로 사용하는 방법.The process according to any one of claims 1 to 3, wherein 5,6-isopropylidene-L-coolonolactone is used as starting material of general formula (II). 제2항 내지 4항중 어느 하나에 있어서, 일반식(I)의 카랄 알데히드와 일반식(Ⅳ)의 아민과의 반응을 유기/수성 2상계에서 수행하는 방법.The process according to any one of claims 2 to 4, wherein the reaction of the aldehyde of formula (I) with the amine of formula (IV) is carried out in an organic / aqueous two-phase system. 제5항에 있어서, 메틸렌클로라이드를 유기/수성 2상계의 유기성분으로 사용하는 방법.The method according to claim 5, wherein methylene chloride is used as an organic component of an organic / aqueous two-phase system. 제2항 내지 6항중 어느 하나에 있어서, R1이 2,4-또는 3,4-또는 3,4-디(저급알콕시)벤질; 디[4-(저급알콕시)페닐] 메틸; 4-(저급알콕시)-페닐; 저급 2-알케닐; CH2-CH(OR8)2[여기에서, R8은 저급알킬을 나타낸다];[여기에서, n은 수 0또는 1을 나타낸다] 중의 어느 하나를 나타내는 일반식(Ⅳ)의 아민을 사용하는 방법.7. The compound of claim 2, wherein R 1 is 2,4- or 3,4- or 3,4-di (lower alkoxy) benzyl; Di [4- (lowalkoxy) phenyl] methyl; 4- (lower alkoxy) -phenyl; Lower 2-alkenyl; CH 2 -CH (OR 8 ) 2 , wherein R 8 represents lower alkyl; Wherein n represents the number 0 or 1, wherein the amine of formula (IV) is used. 제3항 내지 7항중 어느 하나에 있어서, 일반식(Ⅶ)의 카복실산의 산 염화물을 사용하는 방법.The method according to any one of claims 3 to 7, wherein an acid chloride of a carboxylic acid of the general formula is used. 제3항 내지 8항중 어느 하나에 있어서, 프탈로일글리신의 반응성 유도체를 사용하는 방법.The method according to any one of claims 3 to 8, wherein a reactive derivative of phthaloylglycine is used. 제1항에 따라 수득한 일반식(I)의 알데히드를 알카리금속 보로수소화물과 반응시키고, 보호그룹 R14를 도입하고, 경우에 따라서, 그룹를 가수분해시킴을 특징으로 하여 다음 일반식(Ⅸ)의 키랄알코올을 제조하는 방법.The aldehyde of general formula (I) obtained according to claim 1 is reacted with an alkali metal borohydride and the protective group R 14 is introduced, optionally with a group Method for producing chiral alcohol of the following general formula (Ⅸ) characterized by hydrolysis. 상기식에서, R12및 R13은 각각 독립적으로 수소를 나타내거나, 함께 그룹[여기에서, R3및 R4는 각각 독립적으로 수소 또는 저급 알킬을 나타내거나, 함께 저급 알킬렌을 나타낸다]을 나타내고 R14는 하이드록실보호그룹을 나타낸다.Wherein R 12 and R 13 each independently represent hydrogen or group together Wherein R 3 and R 4 each independently represent hydrogen or lower alkyl or together represent lower alkylene, and R 14 represents a hydroxyl protecting group. 제1항에 따라 수득한 일반식(I)의 알데히드를 알카리 금속 보로수소화물과 반응시킴을 특징으로 하여 다음 일반식(I)의 키랄 알코올을 제조하는 방법.A method for preparing chiral alcohol of the following general formula (I), characterized by reacting an aldehyde of general formula (I) obtained according to claim 1 with an alkali metal borohydride. 상기식에서, R3및 R4는 상기 정의한 것과 같다.Wherein R 3 and R 4 are as defined above. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019840000917A 1983-02-25 1984-02-24 Method for preparing chiral aldehyde KR840008022A (en)

Applications Claiming Priority (2)

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CH106183 1983-02-25
CH1061/83 1983-02-25

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KR840008022A true KR840008022A (en) 1984-12-12

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JP (1) JPS59172484A (en)
KR (1) KR840008022A (en)
ZA (1) ZA841193B (en)

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JPS59172484A (en) 1984-09-29
ZA841193B (en) 1984-10-31

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