KR970705546A - 베타-아미노 알콜의 제조법(Process for producing bata-amino alcohol) - Google Patents

베타-아미노 알콜의 제조법(Process for producing bata-amino alcohol)

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Publication number
KR970705546A
KR970705546A KR1019970701302A KR19970701302A KR970705546A KR 970705546 A KR970705546 A KR 970705546A KR 1019970701302 A KR1019970701302 A KR 1019970701302A KR 19970701302 A KR19970701302 A KR 19970701302A KR 970705546 A KR970705546 A KR 970705546A
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South Korea
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formula
acid
phenyl
lower alkyl
benzyl
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KR1019970701302A
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English (en)
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마티아스 코텐한
칼하인쯔 드라오쯔
한스 힐페르트
Original Assignee
클라우스너 프리돌린, 보러 롤란트
에프. 호프만-라 로슈 아게
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Publication of KR970705546A publication Critical patent/KR970705546A/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

3(S)-[저급 알콕시 카보닐 아미노, 페녹시 카보닐 아미노 또는 벤빌 옥시카보닐 아미노]-2-하이드록시-4-페닐 부티르산을 거쳐 2-[3-(S)-아미노-2-(R)-하이드록실-4-페닐 부틸]-N-3급 부틸 테카하이드로-(4aS, 8aS)-이소퀴놀린-e(S)-카복스아미드를 제조하는 방법 및 그 산을 제조하는 방법.

Description

베타-아미노 알콜의 제조법(Process for producing bata-amino alcohol)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (4)

  1. 하기 화학식(2)의 L-페닐알라닌을 프탈산 무수물과 반응시키는 단계 a), 생성된 다음 화학식(3)의 3-페닐-2(S)-프탈이미도프로피온산을 상응하는 산클로라이드로 전환시키는 단계, b) 생성된 다음 화학식(4)의 3-페닐-2(S)-프탈이미도프로피온산 클로라이드를 환원시키는 단계, c) 생성된 다음 화학식(5)의 3-페닐-2(S)-프탈이미도프로판-1-알을 화학식(6)의 1-시아노-3-페닐-2(S)-프탈이미도프로판-1-올로 전환시키는 단계, d) 생성된 다음 화학식(6)의 니트릴을 가수분해하는 단계, e) 형성된 다음 화학식(7) 의 3(S)-아미노-2-하이드록시-4-페닐부티르산을 클로로 포름산의 저급 알킬 에스테르 또는 페닐 또는 벤질 에스테르와 반응시키는 단계, f) 생성 다음 화학식 (8)의 3(S)-[저급 알콕시카보닐아미노-, 페닐옥시카보닐아미노- 또는 벤질옥시카보닐아미노]-2-하이드록시-4-페닐부티르산을 폐환시키는 단계, g) 생성된 다음 화학식(9)의 (4S, 5S)-4-벤질-2-옥소-옥사졸리딘-5-카복실산을 저급 알칸올을 사용하여 에스테르화시키는 단계, h) 생성된 다음 화학식(10)의 (4S,5S)-4-벤질-2-옥소-옥사졸리딘-5-카복실산 저급 알킬 에스테르를 환원시키는 단계, i) 생성된 다음 화학식(11)의 (4S,5S)-4-벤질-5-하이드록시메틸옥사졸리딘-2-온을 염기의 존재하에 화학식 R2-SO2C1 의 설폰산 클로라이드(여기서, R2는 저급 알킬, 페닐 또는 할로겐, 저급 알킬 또는 니트로에 의해 일치환되거나 이치환된 페닐이다)와 반응시키는 단계, j) 생성된 다음 화학식(12)의 설폰산 에스테르를 염기의 존재하에 다음 화학식(13)의 N-3급-부틸-데카하이드로-(4aS, 8aS)-이소퀴놀린-3(S)-카복스아미드와 반응시키는 단계, k)및 생성된 화학식(14)의 2-[(4S,5R)-4-벤질-2-옥소-옥사졸리딘-5-일 메틸]-N-3급-부틸-테카하이드로-(4aS,8aS)-이소퀴놀린-3(S)-카복스아미드를 염기로 처리하는 단계, i)을 포함하여, 다음 화학식(1)의 2-[3(S)-아미노-2(R)-하이드록시-4-페닐부틸]-N-3급-부틸-데카하이드로-(4aS,8aS)-이소퀴놀린-3(S)-카복스아미드를 제조하는 방법.
    상기 화학식(8), (10) 및 (12)에서, R은 저급 알킬, 페닐 또는 벤질이고, R1은 저급 알킬이며, R2는 저급 알킬, 페닐 또는 할로겐, 저급 알킬 또는 니트로에 의해 일치환되거나 이치환된 페닐이다.
  2. 다음 화학식(6)의 1-시아노-3-페닐-2(S)-프탈이미도프로판-1-올을 가수분해시키는 단계, a) 및 형성된 다음 화학식(7)의 3(S)-아미노-2-하이드록시-4-페닐부티르산을 클로로포름산의 저급 알킬 에스테르, 또는 페닐 또는 벤질 에스테르와 반응시키는 단계, b) 를 포함하여, 다음 화학식(8)의 3(S)-[저급 알콕시 카보닐아미노-, 페녹시카보닐아미노- 또는 벤질옥시카보닐아미노]-2-하이드록시-4-페닐부티르산을 제조하는 방법.
    상기 화학식(8)에서, R은 저급 알킬, 페닐 또는 벤질이다.
  3. 제1항에 있어서, 화학식(3)의 화합물에서 출방하여 단계 b)에서 h)까지를 중간 생성물을 분리하지 않고 수행하고, 단계 e)에서 가수분해를 염산 매질 속에서 수행함을 특징으로 하여, 다음 화학식(9)의 (4S,5S)-4-벤질-2-옥소-옥사졸리딘-5-카복실산을 제조하는 방법.
  4. 다음 화학식(6)의 1-시아노-3-페닐-2(S)-프탈이미도프로판-1-올을 저급 알칸올의 존재하에 강산을 사용하여 다음 화학식(6′)의 이미노 에테르의 염으로 전환시키는 단계, a) 다음 화학식(6′)의 이미노 에테르의 염을 가수분해하는 단계, b) 생성된 다음 화학식(15)의 α-하이드록시산 에스테르를 먼저 염을 사용하고 이어서 강산을 사용하여 다음 화학식(16)의 α-하이드록시-β-아미노산 에스테르로 전환시키는 단계, c) 다음 화학식(16)의 α-하이드록시-β-아미노산을 클로로포름산의 저급 알킬 에스테르 또는 페닐 또는 벤질 에스테르와 반응시키는 단계, d) 및 생성된 다음 화학식(17)의 3(S)-[저급 알콕시카보닐아미노-, 페녹시카보닐아미노- 또는 벤질옥시카보닐아미노]-2(S)-하이드록시-4-페닐부티르산 저급 알킬 에스테르를 폐환시키는 단계, e) 를 포함하여, 다음 화학식(9)의 (4S,5S)-4-벤질-2-옥소-옥사졸리딘-5-카복실산을 제조하는 방법.
    상기 화학식 (6′), (16) 및 (17)에서 R1은 저급 알킬이고, R 은 저급 알킬, 페닐 또는 벤질이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019970701302A 1994-09-03 1995-08-17 베타-아미노 알콜의 제조법(Process for producing bata-amino alcohol) KR970705546A (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4431530A DE4431530C2 (de) 1994-09-03 1994-09-03 Verfahren zur Herstellung von 2-[3(S)-Amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isochinolin-3(S)-carboxamid
DEP4431530.9 1994-09-03
PCT/EP1995/003280 WO1996007642A1 (de) 1994-09-03 1995-08-17 VERFAHREN ZUR HERSTELLUNG EINES β-AMINOALKOHOLS

Publications (1)

Publication Number Publication Date
KR970705546A true KR970705546A (ko) 1997-10-09

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KR1019970701302A KR970705546A (ko) 1994-09-03 1995-08-17 베타-아미노 알콜의 제조법(Process for producing bata-amino alcohol)

Country Status (11)

Country Link
US (2) US5859248A (ko)
EP (1) EP0778827B1 (ko)
JP (1) JPH10505069A (ko)
KR (1) KR970705546A (ko)
CN (1) CN1159185A (ko)
AT (1) ATE210646T1 (ko)
CA (1) CA2198460A1 (ko)
DE (2) DE4431530C2 (ko)
DK (1) DK0778827T3 (ko)
ES (1) ES2168382T3 (ko)
WO (1) WO1996007642A1 (ko)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4431530C2 (de) * 1994-09-03 2002-01-31 Degussa Verfahren zur Herstellung von 2-[3(S)-Amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isochinolin-3(S)-carboxamid
JP2002080435A (ja) * 2000-06-26 2002-03-19 Kanegafuchi Chem Ind Co Ltd ３−アミノ−２−ヒドロキシプロピオン酸誘導体の製造法
JP2002371044A (ja) * 2001-04-11 2002-12-26 Ajinomoto Co Inc β−アミノ−α−ヒドロキシカルボン酸の製造方法
US6792281B2 (en) * 2002-06-28 2004-09-14 Motorola, Inc. Method and system for patching dispatch calling parties together
WO2006096994A1 (en) * 2005-03-16 2006-09-21 The University Of Manitoba Fluorous oxazolidinone chiral auxiliary compounds and methods of manufacture

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL58849A (en) * 1978-12-11 1983-03-31 Merck & Co Inc Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them
JPH06184069A (ja) * 1991-11-19 1994-07-05 Lonza Ag α−ヒドロキシ−β−アミノカルボン酸の製造方法
US5455353A (en) * 1993-03-24 1995-10-03 Hoffmann-La Roche Inc. 4-(benzyl-2-oxo-oxazolidin-5 ylmethyl)N tertbutyl-decahydroisoquinoline-3-carboxamides
DE4431530C2 (de) * 1994-09-03 2002-01-31 Degussa Verfahren zur Herstellung von 2-[3(S)-Amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-decahydro-(4aS,8aS)-isochinolin-3(S)-carboxamid

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Publication number Publication date
DE59509946D1 (de) 2002-01-24
ATE210646T1 (de) 2001-12-15
ES2168382T3 (es) 2002-06-16
EP0778827B1 (de) 2001-12-12
US5994555A (en) 1999-11-30
CA2198460A1 (en) 1996-03-14
DK0778827T3 (da) 2002-04-08
WO1996007642A1 (de) 1996-03-14
US5859248A (en) 1999-01-12
EP0778827A1 (de) 1997-06-18
DE4431530A1 (de) 1996-03-14
CN1159185A (zh) 1997-09-10
JPH10505069A (ja) 1998-05-19
DE4431530C2 (de) 2002-01-31

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