KR850008484A - 광학적 활성 알파-아릴알카노산의 제조방법 - Google Patents

광학적 활성 알파-아릴알카노산의 제조방법 Download PDF

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KR850008484A
KR850008484A KR1019850002311A KR850002311A KR850008484A KR 850008484 A KR850008484 A KR 850008484A KR 1019850002311 A KR1019850002311 A KR 1019850002311A KR 850002311 A KR850002311 A KR 850002311A KR 850008484 A KR850008484 A KR 850008484A
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기오르다노 클라우디오
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알베르토 잠본
잠본 에스. 피. 에이
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    • C07—ORGANIC CHEMISTRY
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
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    • C07—ORGANIC CHEMISTRY
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    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
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Abstract

내용 없음

Description

광학적 활성 알파-아릴알카노산의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반식(A-1)의 케탈을 케탈그룹에 대한 알파-위치에서 아키랄 할로겐화제로 할로겐화시켜 2개의 에난티오머적으로 순수한 에피머중 한가지로 주로 또는 다량 이루어진 하기 일반식(A-2)의 알파-할로-케탈의 에피머 혼합물을 수득하고, 수득된 혼합물을 1단계 또는 2단계 공정에 의해 출발물질인 알파-할로-케탈의 에피머비에 거의 상응하는 에난티오머비를 갖는 알파-아릴알카노산의 에난티오머 혼합물로 전위시키고, 필요시 하기 일반식(C)의 중간체 화합물을 분리시킨 다음, 가수분해시킴을 특징으로 하는, 광학적 활성알파-아릴알카노산의 에난티오 선택적 제조방법:
    상기식에서, Ar은 임의로 치환된 아릴이고, R은 직쇄 또는 축쇄 C1-C4알킬이며, R1및 R2는 동일 또는 상이할 수 있으며, 하이드록시, O-M+, OR3또는 NR4R5그룹이고, 여기서 R3는 C1-C24알킬, C3-C6시클로알킬, 페닐 또는 젠질이며, M+는 알칼리 금속의 양이온이고, R4및 R5는 동일 또는 상이할 수 있으며, 수소원자, C1-C4알킬, C5-C6시클로알킬 또는 -(CH2)n-CH2OH그룹(여기서 n은 1,2 또는 3이다)이거나, R4및 R5가 함께 -(CH2)m-그룹(여기서 m은 4 또는 5이다) 또는 -CH2-CH2-R7-CH2-CH2-그룹(여기서 R7은 산소원자, NH 그룹 또는 N-C1-C4알킬그룹이다)을 형성하고, C+는 둘다(R) 또는 (S)배위를 가지며, X는 Cl, Br 또는 I이고, R6는 하이드록시, Cl, Br, I 또는 아실라디칼이다.
  2. 제1항에 있어서, 언급된 할로겐화 반응을, -40° 내지 30℃에서 불활성 유기용매의 존재하에, 브롬, 4급 암모늄 퍼할라이드, 설퍼릴 클로라이드, 염화 제2구리, 브롬화 제2구리, N-클로로선식이미드, 피리딘 퍼브로마이드, 피롤리돈 퍼브로마이드, 헥사클로로-2,4-시클로헥사디엔은, 요오드 및 염화요오드로부터 선택된 아키랄 할로겐화 시스템을 사용하여 수행하는 방법.
  3. 제2항에 있어서, 언급된 할로겐화제가 브롬인 방법.
  4. 제1항에 있어서, 언급된 알파-할로-케탈의 에피머 혼합물의 전위를 20° 내지 100℃에서 산성조건하에 수-함유 매질중에서 1단계 공정으로 수행하여 출발물질인 알파-할로-케탈의 에피머 비보다 더 높은 에난티오머 비를 갖는 상응하는 알파-아릴알카노산을 수득하는 방법.
  5. 제4항에 있어서, 언급된 전위를 pH4 내지 6에서 수행하는 방법.
  6. 제1항에 있어서, 언급된 알파-할로-케탈의 디아스테레오머 혼합물의 전위를 알콜 및 글리콜이 함유되지 않은 유기매질중에서 처리하여 2단계 공정으로 수행하는 방법.
  7. 제1항에 있어서, 하기 일반식(B-1)의 케탈을 케탈그룹에 대한 알파-위치에서 아키랄 할로겐화제로 할로겐화시켜 X가 결합된 탄소원자가(S) 배위를 갖는 에피머로 주로 또는 다량 이루어진 하기 일반식(B-2)의 알파-할로-케탈의 에피머 혼합물을 수득하고, 수득된 혼합물을 1단계 또는 2단계 공정에 의해 출발물질인 케탈의 에피머 비와 거의 동일하거나 더 높은 에난티오머비를 갖는 상응하는 알파-아릴알카노산으로 전위시키고, 필요시 하기 일반식(D)의 중간체 화합물을 분리시킨 다음, 가수분해 시키고, Y가 할로겐인 경우에 가수소 분해시키는 방법:
    상기식에서, R1, R2및 R6는 제1항에서와 동일하고, X는 염소, 브롬 또는 요오드이며, Y는 수소, 염소 또는 브롬이고, Z는 수소, 메틸 또는 알칼리금속이며, C+는 모두 (R) 배위를 갖는다.
  8. 제7항에 있어서, 언급된 할로겐화 반응을, -40°내지 30°에서 불활성 유기용매의 존재하에 브롬을 사용하여 수행하는 방법.
  9. 제7항에 있어서, 언급된 전위를 20° 내지 100℃에서 산성조건하에 수-함유 매질중에서 1단계 공정으로 수행하는 방법.
  10. 제7항에 있어서, 언급된 전위를 알콜 및 글리콜이 함유되지 않은 유기 매질중에서 중간체 화합물(D)를 분리시킨 다음 가수분해 시킴으로써 2단계로 수행하는 방법.
    ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850002311A 1984-04-06 1985-04-06 광학적 활성 알파-아릴알카노산의 제조방법 KR920007223B1 (ko)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
IT8407204A IT1214809B (it) 1984-04-06 1984-04-06 Intermedi utili per la sintesi di acidi carbossilici.
IT7204A/84 1984-04-06
IT7206A/84 1984-08-06
IT8407207A IT1207420B (it) 1984-08-06 1984-08-06 Acidi carbossilici. procedimento per la preparazione di
IT07206/84A IT1199447B (it) 1984-08-06 1984-08-06 Intermedi utili per la sintesi di acidi carbossilici
IT7207A/84 1984-08-06

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KR850008484A true KR850008484A (ko) 1985-12-18
KR920007223B1 KR920007223B1 (ko) 1992-08-28

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AT (2) ATE39691T1 (ko)
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JPS5810525A (ja) * 1981-06-15 1983-01-21 Sagami Chem Res Center 光学活性な１−芳香族基置換−１−アルカノン類の製造方法
IT1190741B (it) * 1982-03-22 1988-02-24 Blaschim Spa Procedimento per preparare esteri dell'acido 2-(6'-metossi-2'-naftil)-propionico
US4623736A (en) * 1982-07-09 1986-11-18 The Upjohn Company Arylalkanoic acid process improvement
DE3362024D1 (en) * 1982-08-06 1986-03-13 Zambon Spa Process for preparing alpha arylalkanoic acids
JPS6071271A (ja) * 1983-09-29 1985-04-23 Fuji Xerox Co Ltd 感熱記録装置
DE3567209D1 (en) * 1984-04-06 1989-02-09 Zambon Spa Optically active ketals, processes for their preparation and their use in the synthesis of apha-arylakanoic acids
JPH0585102A (ja) * 1991-09-24 1993-04-06 Nissan Motor Co Ltd トルクチユーブ装置

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AU575927B2 (en) 1988-08-11
FI91528B (fi) 1994-03-31
US4697036A (en) 1987-09-29
HU198439B (en) 1989-10-30
JPH0791214B2 (ja) 1995-10-04
CA1282410C (en) 1991-04-02
GR850846B (ko) 1985-11-25
JP2700024B2 (ja) 1998-01-19
KR850007594A (ko) 1985-12-07
AU577362B2 (en) 1988-09-22
ES8707490A1 (es) 1987-08-01
FI851318A0 (fi) 1985-04-02
FI851318L (fi) 1985-10-07
NO170685C (no) 1992-11-18
NO851350L (no) 1985-10-07
NO170685B (no) 1992-08-10
ES551476A0 (es) 1987-05-01
JPH06100491A (ja) 1994-04-12
FI851317L (fi) 1985-10-07
DE3567209D1 (en) 1989-02-09
IE58258B1 (en) 1993-08-25
EP0158913B1 (en) 1988-07-20
ES8705415A1 (es) 1987-05-01
JPH06116201A (ja) 1994-04-26
ES542641A0 (es) 1986-12-16
JP2700023B2 (ja) 1998-01-19
PT80244A (en) 1985-05-01
JPH0859552A (ja) 1996-03-05
EP0158255B1 (en) 1989-01-04
NO169385B (no) 1992-03-09
AU4084085A (en) 1985-10-10
CA1281029C (en) 1991-03-05
JPH0776193B2 (ja) 1995-08-16
KR920007223B1 (ko) 1992-08-28
DK166272C (da) 1993-10-25
US4855464A (en) 1989-08-08
DE3563848D1 (en) 1988-08-25
JPH0867652A (ja) 1996-03-12
EP0158255A3 (en) 1986-09-03
FI91393B (fi) 1994-03-15
JPS60228440A (ja) 1985-11-13
YU43686B (en) 1989-10-31
IE58032B1 (en) 1993-06-16
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ATE39691T1 (de) 1989-01-15
HUT37931A (en) 1986-03-28
DK149885A (da) 1985-10-07
EP0158255A2 (en) 1985-10-16
YU57985A (en) 1987-12-31
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PT80244B (en) 1987-04-23
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ATE35810T1 (de) 1988-08-15
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ES554936A0 (es) 1987-07-01
US4734507A (en) 1988-03-29
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IE850880L (en) 1985-10-06
IE850879L (en) 1985-10-06
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HU197711B (en) 1989-05-29
JPH07107018B2 (ja) 1995-11-15
FI91528C (fi) 1994-07-11
ES8706661A1 (es) 1987-07-01
ES8802295A1 (es) 1988-05-01
FI91393C (fi) 1994-06-27
JPS60228441A (ja) 1985-11-13
KR920010927B1 (ko) 1992-12-24
PT80243B (en) 1987-04-28
NO169385C (no) 1992-06-17
JPH0784457B2 (ja) 1995-09-13
YU57085A (en) 1987-12-31
DK149785A (da) 1985-10-07
JPH06100498A (ja) 1994-04-12
YU43942B (en) 1989-12-31
ES8701748A1 (es) 1986-12-16
EP0158913A2 (en) 1985-10-23
US4888433A (en) 1989-12-19
DK166876B1 (da) 1993-07-26
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MX169453B (es) 1993-07-06
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PT80243A (en) 1985-05-01
NO851349L (no) 1985-10-07

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