KR970015583A - (S) -β-하이드록시-γ-부티로락톤의 제조방법 - Google Patents

(S) -β-하이드록시-γ-부티로락톤의 제조방법 Download PDF

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Publication number
KR970015583A
KR970015583A KR1019960029667A KR19960029667A KR970015583A KR 970015583 A KR970015583 A KR 970015583A KR 1019960029667 A KR1019960029667 A KR 1019960029667A KR 19960029667 A KR19960029667 A KR 19960029667A KR 970015583 A KR970015583 A KR 970015583A
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KR
South Korea
Prior art keywords
hydroxy
butyrolactone
solvent
structural formula
following structural
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KR1019960029667A
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English (en)
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KR100407645B1 (ko
Inventor
파비오 기아네씨
안젤리스 프란체스코 데
Original Assignee
알도 파시
시그마타우 인두스트리에 파르마슈티케 리우니테 에스. 페. 에이.
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Publication of KR970015583A publication Critical patent/KR970015583A/ko
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Seasonings (AREA)

Abstract

본 발명은 (S)-β-하이드록시-γ-부티로락톤의 제조방법에 관한 것으로서, 더욱 상세하기로는 라세미 혼합물의 분리방법에 의해 (R)-카르니틴을 제조하는 공정에서 얻어지는 값싼 폐부산물을 사용하고 몇몇 유기합성공정을 이용하여 광범위한 중간체 화합물로 사용되고 있는 (S)-β-하이드록시-γ-부티로락톤을 제조하는 방법에 관한 것이다.

Description

(S)-β-하이드록시-γ-부티로락톤의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (5)

  1. 다음 반응식에 의해 (S)-카르니틴을 직접 전환시켜 다음 구조식(Ⅰ)로 표시되는 (S)-β-하이드록시-γ부티로락톤의 제조하되 (S)-카르니틴 내부염을 불활성용매에 녹인 다음, 반응용액을 100~190℃에서 0.5~5시간 방치한 후, 감압증류시키는 것을 특징으로 하는 다음 구조식(Ⅰ)로 표시되는 (S)-β-하이드록시-γ-부티로락톤의 제조방법.
  2. 다음 반응식에 의해 (S)-카르니틴을 직접 전환시켜 다음 구조식(Ⅰ)로 표시되는 (S)-β-하이드록시-γ-부티로락톤을 제조하되 (S)-카르니틴염과 동물량(equimolar amount)의 염기를 불활성용매에 녹인 다음, 반응용액을 100~190℃에서 0.5~5시간 후, 감압증류시키는 것을 특징으로 하는 다음 구조식(Ⅰ)로 표시되는 (S)-β-하이드록시-γ-부티로락톤의 제조방법.
    상기 식에서 X-는 특정 음이온이다.
  3. 제2항에 있어서, 상기 염기(base)로는 NaHCO3, NaOH 및 Et3N 중에서 선택된 것을 사용하는 것을 특징으로 하는 (S)-β-하이드록시-γ-부티로락톤의 제조방법.
  4. 제1항 또는 제2항에 있어서, 상기 용매로는 DMSO 및 DMF 중에서 선택된 비양성자성의 이중극성용매(anaprotic dipolar solvent)를 사용하는 것을 특징으로 하는 (S)-β-하이드록시-γ-부티로락톤의 제조방법.
  5. 제1항 또는 제2항에 있어서, 상기 용매로서 CH3CN/H2O 혼합용매를 사용하고, 80℃ 내지 용액의 환류온도에서 1~7일동안 반응시키는 것을 특징으로 하는 (S)-β-하이드록시-γ-부티로락톤의 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019960029667A 1995-09-29 1996-07-23 (S)-β-하이드록시-γ-부티로락톤의제조방법 KR100407645B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITRM95A000652 1995-09-29
IT95RM000652A IT1276207B1 (it) 1995-09-29 1995-09-29 Procedimento per la preparazione del (s)-b-idrossi-gamma- butirrolattone

Publications (2)

Publication Number Publication Date
KR970015583A true KR970015583A (ko) 1997-04-28
KR100407645B1 KR100407645B1 (ko) 2004-03-18

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KR1019960029667A KR100407645B1 (ko) 1995-09-29 1996-07-23 (S)-β-하이드록시-γ-부티로락톤의제조방법

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US (1) US5714619A (ko)
EP (1) EP0765876B1 (ko)
JP (1) JP4012588B2 (ko)
KR (1) KR100407645B1 (ko)
AT (1) ATE174333T1 (ko)
CA (1) CA2181012A1 (ko)
DE (1) DE69601116T2 (ko)
DK (1) DK0765876T3 (ko)
ES (1) ES2126969T3 (ko)
GR (1) GR3029537T3 (ko)
IT (1) IT1276207B1 (ko)
ZA (1) ZA968127B (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000065995A (ko) * 1999-04-12 2000-11-15 박영구 키랄 3-히드록시-γ-부티로락톤의 제조방법

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1297120B1 (it) * 1997-12-16 1999-08-03 Sigma Tau Ind Farmaceuti Procedimento per la produzione di (r)-3-idrossi-4-butirrolattone utile nella preparazione della (r)-carnitina
JP4390394B2 (ja) 1998-12-11 2009-12-24 ダイセル化学工業株式会社 イミド化合物触媒を用いた有機化合物の製造法
CN104961711B (zh) * 2015-07-23 2017-03-08 沧州那瑞化学科技有限公司 （s）‑3‑羟基四氢呋喃和（r）‑3‑羟基四氢呋喃的制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3087325B2 (ja) * 1991-02-21 2000-09-11 チッソ株式会社 光学活性化合物とその製造法
IT1256705B (it) * 1992-12-21 1995-12-12 Sigma Tau Ind Farmaceuti Procedimento per la preparazione di l-(-)-carnitina a partire da un prodotto di scarto avente opposta configurazione.
IT1261231B (it) * 1993-04-08 1996-05-09 Sigma Tau Ind Farmaceuti Procedimento migliorato per la preparazione di l-(-)-carnitina a partire da un prodotto di scarto avente opposta configurazione.
IT1261230B (it) * 1993-04-08 1996-05-09 Sigma Tau Ind Farmaceuti Procedimento migliorato per la preparazione di l-(-)-carnitina a partire da suoi precursori aventi opposta configurazione.
IT1261489B (it) * 1993-07-29 1996-05-23 Sigma Tau Ind Farmaceuti Procedimento per la produzione di r amminocarnitina e s amminocarnitina.
US5473104A (en) * 1994-09-13 1995-12-05 Neurocrine Biosciences, Inc. Process for the preparation of L-carnitine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000065995A (ko) * 1999-04-12 2000-11-15 박영구 키랄 3-히드록시-γ-부티로락톤의 제조방법

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Publication number Publication date
ES2126969T3 (es) 1999-04-01
ITRM950652A1 (it) 1997-03-29
GR3029537T3 (en) 1999-06-30
ZA968127B (en) 1997-04-21
ITRM950652A0 (ko) 1995-09-29
JP4012588B2 (ja) 2007-11-21
JPH09110851A (ja) 1997-04-28
ATE174333T1 (de) 1998-12-15
DK0765876T3 (da) 1999-08-16
EP0765876A1 (en) 1997-04-02
EP0765876B1 (en) 1998-12-09
IT1276207B1 (it) 1997-10-27
US5714619A (en) 1998-02-03
DE69601116D1 (de) 1999-01-21
CA2181012A1 (en) 1997-03-30
KR100407645B1 (ko) 2004-03-18
DE69601116T2 (de) 1999-05-06

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