WO2010053050A1 - O-alkylsérine et procédé de production de n-benzyl-o-alkysérine - Google Patents

O-alkylsérine et procédé de production de n-benzyl-o-alkysérine Download PDF

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Publication number
WO2010053050A1
WO2010053050A1 PCT/JP2009/068657 JP2009068657W WO2010053050A1 WO 2010053050 A1 WO2010053050 A1 WO 2010053050A1 JP 2009068657 W JP2009068657 W JP 2009068657W WO 2010053050 A1 WO2010053050 A1 WO 2010053050A1
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WO
WIPO (PCT)
Prior art keywords
alkylserine
formula
acid
benzyl
compound
Prior art date
Application number
PCT/JP2009/068657
Other languages
English (en)
Japanese (ja)
Inventor
啓明 直原
章 西山
進 天野
雅俊 大貫
増俊 野尻
直明 田岡
Original Assignee
株式会社カネカ
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 株式会社カネカ filed Critical 株式会社カネカ
Publication of WO2010053050A1 publication Critical patent/WO2010053050A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/38—Separation; Purification; Stabilisation; Use of additives
    • C07C227/40—Separation; Purification
    • C07C227/42—Crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/04—Alpha- or beta- amino acids
    • C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine

Abstract

La présente invention concerne une O-alkylsérine qui peut être utilisée en tant qu'intermédiaire pharmaceutique. L'invention concerne également un procédé de production d'une N-benzyl-O-alkylsérine, qui est un composé pouvant être utilisé pour la production, à l'échelle industrielle, de ladite O-alkylsérine, à partir d'un matériau de départ facilement disponible et en utilisant un réactif peu onéreux, et ce de façon simple et très efficace. Un composé de formule (3) est hydrolysé pour donner une solution réactionnelle. La N-benzyl-O-alkylsérine est isolée sous la forme de cristaux directement à partir de la solution réactionnelle. De façon particulièrement préférée, un dérivé de la 1-benzylaziridine, qui est un composé facilement disponible, est soumis à une réaction d'ouverture de cycle avec un alcool et un acide de Brönsted pour obtenir un composé de formule (3). La N-benzyl-O-alkysérine est débenzylée pour obtenir la O-alkysérine.
PCT/JP2009/068657 2008-11-04 2009-10-30 O-alkylsérine et procédé de production de n-benzyl-o-alkysérine WO2010053050A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008-283435 2008-11-04
JP2008283435 2008-11-04

Publications (1)

Publication Number Publication Date
WO2010053050A1 true WO2010053050A1 (fr) 2010-05-14

Family

ID=42152860

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2009/068657 WO2010053050A1 (fr) 2008-11-04 2009-10-30 O-alkylsérine et procédé de production de n-benzyl-o-alkysérine

Country Status (1)

Country Link
WO (1) WO2010053050A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020095983A1 (fr) 2018-11-07 2020-05-14 中外製薬株式会社 Procédé de production d'un dérivé de sérine o-substitué
US11492369B2 (en) 2017-12-15 2022-11-08 Chugai Seiyaku Kabushiki Kaisha Method for producing peptide, and method for processing bases
US11542299B2 (en) 2017-06-09 2023-01-03 Chugai Seiyaku Kabushiki Kaisha Method for synthesizing peptide containing N-substituted amino acid
US11732002B2 (en) 2018-11-30 2023-08-22 Chugai Seiyaku Kabushiki Kaisha Deprotection method and resin removal method in solid-phase reaction for peptide compound or amide compound, and method for producing peptide compound
WO2024024965A1 (fr) * 2022-07-29 2024-02-01 中外製薬株式会社 Procédé de production d'un dérivé de sérine o-substitué
US11891457B2 (en) 2011-12-28 2024-02-06 Chugai Seiyaku Kabushiki Kaisha Peptide-compound cyclization method

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4927858B1 (fr) * 1968-12-14 1974-07-22
JPS57159747A (en) * 1981-03-27 1982-10-01 Kenji Okawa Synthesis of amino acid derivative
JPS58172352A (ja) * 1982-04-05 1983-10-11 Mitsui Toatsu Chem Inc セリンの分離方法
JPH10251209A (ja) * 1997-03-07 1998-09-22 Nof Corp （メタ）アクリル酸セリンエステル、製造方法、共重合体および生体適合性材料
JP2006115729A (ja) * 2004-10-20 2006-05-11 Daicel Chem Ind Ltd 光学活性β−ヒドロキシアミノ酸の晶析方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4927858B1 (fr) * 1968-12-14 1974-07-22
JPS57159747A (en) * 1981-03-27 1982-10-01 Kenji Okawa Synthesis of amino acid derivative
JPS58172352A (ja) * 1982-04-05 1983-10-11 Mitsui Toatsu Chem Inc セリンの分離方法
JPH10251209A (ja) * 1997-03-07 1998-09-22 Nof Corp （メタ）アクリル酸セリンエステル、製造方法、共重合体および生体適合性材料
JP2006115729A (ja) * 2004-10-20 2006-05-11 Daicel Chem Ind Ltd 光学活性β−ヒドロキシアミノ酸の晶析方法

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11891457B2 (en) 2011-12-28 2024-02-06 Chugai Seiyaku Kabushiki Kaisha Peptide-compound cyclization method
US11542299B2 (en) 2017-06-09 2023-01-03 Chugai Seiyaku Kabushiki Kaisha Method for synthesizing peptide containing N-substituted amino acid
US11787836B2 (en) 2017-06-09 2023-10-17 Chugai Seiyaku Kabushiki Kaisha Method for synthesizing peptide containing N-substituted amino acid
US11492369B2 (en) 2017-12-15 2022-11-08 Chugai Seiyaku Kabushiki Kaisha Method for producing peptide, and method for processing bases
WO2020095983A1 (fr) 2018-11-07 2020-05-14 中外製薬株式会社 Procédé de production d'un dérivé de sérine o-substitué
KR20210088619A (ko) 2018-11-07 2021-07-14 추가이 세이야쿠 가부시키가이샤 O-치환 세린 유도체의 제조 방법
US11732002B2 (en) 2018-11-30 2023-08-22 Chugai Seiyaku Kabushiki Kaisha Deprotection method and resin removal method in solid-phase reaction for peptide compound or amide compound, and method for producing peptide compound
WO2024024965A1 (fr) * 2022-07-29 2024-02-01 中外製薬株式会社 Procédé de production d'un dérivé de sérine o-substitué

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