KR940002218A - Method for preparing N-benzyloxycarbonyl-N'-hydroxymethyl-α-L-aspartyl-L-phenylalaninemethyl ester - Google Patents

Method for preparing N-benzyloxycarbonyl-N'-hydroxymethyl-α-L-aspartyl-L-phenylalaninemethyl ester Download PDF

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Publication number
KR940002218A
KR940002218A KR1019920013418A KR920013418A KR940002218A KR 940002218 A KR940002218 A KR 940002218A KR 1019920013418 A KR1019920013418 A KR 1019920013418A KR 920013418 A KR920013418 A KR 920013418A KR 940002218 A KR940002218 A KR 940002218A
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South Korea
Prior art keywords
preparing
oxazolidinone
aspartyl
benzyloxycarbonyl
hydroxymethyl
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KR1019920013418A
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Korean (ko)
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KR960009053B1 (en
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최경은
주대권
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유영학
주식회사 미원
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Priority to KR92013418A priority Critical patent/KR960009053B1/en
Publication of KR940002218A publication Critical patent/KR940002218A/en
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Publication of KR960009053B1 publication Critical patent/KR960009053B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
    • C07K5/0613—Aspartame
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
    • Y10S530/801—Peptide sweetners

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Peptides Or Proteins (AREA)

Abstract

아스파탐 제조를 위한 중간체인 N-벤질옥시카르보닐-N'-히드록시메틸-α-L-아스파르틸-L-페닐알라닌메틸 에스테르의 제조하는 방법에 관한 것으로서 N-보호된 아스파르트산을 산 촉매하에서 파라포름알데히드와 반응시켜 5-옥사졸리디논을 만들고 다시 L-페닐알라닌 메틸 에스테르 용액과 반응시키는 것에 관한 것이다.A process for preparing N-benzyloxycarbonyl-N'-hydroxymethyl-α-L-aspartyl-L-phenylalaninemethyl ester, an intermediate for preparing aspartame, wherein N-protected aspartic acid is subjected to an acid catalyst. Reaction with paraformaldehyde to form 5-oxazolidinone and again with L-phenylalanine methyl ester solution.

본 발명의 방법을 사용할 경우, α,β체의 분리 공정이 없이, 높은 수율로 α-아스파탐 중간체를 제조할 수 있다.When using the method of the present invention, α-aspartame intermediate can be prepared in high yield without the process of separating α, β bodies.

Description

N-벤질옥시카르보닐-N'-히드록시 메틸-알파-α-L-아스파르틸-L-페닐알라닌메틸 에스테르의 제조방법Method for preparing N-benzyloxycarbonyl-N'-hydroxy methyl-alpha-α-L-aspartyl-L-phenylalaninemethyl ester

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

Claims (3)

N-보호된 아스파르트산을 산 촉매하에서 파라포름알데히드와 반응시켜 5-고리화합물인 5-옥사졸리디논을 만들어 L-페닐알라닌 메틸 에스테르 용액과 반응시킴을 특징으로 하는, N-벤질옥시카르보닐-N'-히드록시메틸-α-L-아스파르틸-L-페닐알라닌메틸 에스테르의 제조하는 방법.N-benzyloxycarbonyl-N, characterized in that N-protected aspartic acid is reacted with paraformaldehyde under an acid catalyst to form 5-ring compound 5-oxazolidinone and reacted with L-phenylalanine methyl ester solution. Process for the preparation of '-hydroxymethyl-α-L-aspartyl-L-phenylalaninemethyl ester. 단, 상기 식에서 Z는 벤질욕시카르보닐기, 포르밀기, 벤조일기이다.However, in the formula, Z is benzyl bath carbonyl group, formyl group, benzoyl group. 제1항에 있어서, 5-옥사졸리디논을 제조할 때 반응용매를 벤젠, 톨루엔, 헥산과 같은 탄화수소; 에틸 아세테이트 및 메틸 아세테이트와 같은 아세테이트; 메틸클로라이드, 클로로포름 같은 할로겐화 탄화수소를 사용하여 제조하는 방법.The method of claim 1, wherein the reaction solvent when preparing 5-oxazolidinone is selected from the group consisting of hydrocarbons such as benzene, toluene, hexane; Acetates such as ethyl acetate and methyl acetate; Process prepared using halogenated hydrocarbons such as methyl chloride, chloroform. 제1항에 있어서, 5-옥사졸리디논의 L-페닐알라닌 메틸에스테르 용액과의 축합반응 온도를 20~45℃로 하여 제조하는 방법.The process according to claim 1, wherein the condensation reaction temperature of 5-oxazolidinone with the L-phenylalanine methyl ester solution is set to 20 to 45 ° C. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR92013418A 1992-07-27 1992-07-27 PROCESS FOR PRODUCING N-BENZYL-OXYCARBONYL-N'-HYDROXYMETHYL-Ñß-L-ASPARTYL-L-PHENYLALANINE METHYLESTER KR960009053B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR92013418A KR960009053B1 (en) 1992-07-27 1992-07-27 PROCESS FOR PRODUCING N-BENZYL-OXYCARBONYL-N'-HYDROXYMETHYL-Ñß-L-ASPARTYL-L-PHENYLALANINE METHYLESTER

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR92013418A KR960009053B1 (en) 1992-07-27 1992-07-27 PROCESS FOR PRODUCING N-BENZYL-OXYCARBONYL-N'-HYDROXYMETHYL-Ñß-L-ASPARTYL-L-PHENYLALANINE METHYLESTER

Publications (2)

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KR940002218A true KR940002218A (en) 1994-02-16
KR960009053B1 KR960009053B1 (en) 1996-07-10

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KR92013418A KR960009053B1 (en) 1992-07-27 1992-07-27 PROCESS FOR PRODUCING N-BENZYL-OXYCARBONYL-N'-HYDROXYMETHYL-Ñß-L-ASPARTYL-L-PHENYLALANINE METHYLESTER

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