JPS5579353A - Preparation of (2s,3r)-3-amino-2-hydroxy-4- phenylbutanoylaminoacetic acid and its intermediate - Google Patents

Preparation of (2s,3r)-3-amino-2-hydroxy-4- phenylbutanoylaminoacetic acid and its intermediate

Info

Publication number
JPS5579353A
JPS5579353A JP15315778A JP15315778A JPS5579353A JP S5579353 A JPS5579353 A JP S5579353A JP 15315778 A JP15315778 A JP 15315778A JP 15315778 A JP15315778 A JP 15315778A JP S5579353 A JPS5579353 A JP S5579353A
Authority
JP
Japan
Prior art keywords
amino
compounds
formula
acid
hydroxy
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
JP15315778A
Other languages
Japanese (ja)
Other versions
JPS6121466B2 (en
Inventor
Tadashi Shirai
Rinzo Nishizawa
Masao Suzuki
Tetsuyuki Saino
Hamao Umezawa
Takaaki Aoyanagi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Kayaku Co Ltd
Original Assignee
Nippon Kayaku Co Ltd
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 Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd
Priority to JP15315778A priority Critical patent/JPS5579353A/en
Priority to GB7940413A priority patent/GB2037754B/en
Priority to CS814806A priority patent/CS221955B2/en
Priority to ES486572A priority patent/ES486572A1/en
Priority to CH5649/81A priority patent/CH653687A5/en
Priority to DK496379A priority patent/DK162288C/en
Priority to HU79NI230A priority patent/HU181920B/en
Priority to GB8200496A priority patent/GB2090595B/en
Priority to CA000340428A priority patent/CA1182125A/en
Priority to NLAANVRAGE7908510,A priority patent/NL188162C/en
Priority to SE7909655A priority patent/SE452888B/en
Priority to DE19792947140 priority patent/DE2947140A1/en
Priority to CS798051A priority patent/CS221953B2/en
Priority to AU53115/79A priority patent/AU530362B2/en
Priority to CH10433/79A priority patent/CH650265A5/en
Priority to IT27487/79A priority patent/IT1194593B/en
Priority to DE2954076A priority patent/DE2954076C2/de
Priority to FR7928830A priority patent/FR2442227A1/en
Priority to AR278992A priority patent/AR227636A1/en
Priority to CH6192/83A priority patent/CH653669A5/en
Priority to US06/096,693 priority patent/US4281180A/en
Priority to FR8010563A priority patent/FR2449078A1/en
Publication of JPS5579353A publication Critical patent/JPS5579353A/en
Priority to US06/211,035 priority patent/US4391986A/en
Priority to FR8113611A priority patent/FR2483409B1/en
Priority to NL8104545A priority patent/NL8104545A/en
Priority to SE8106084A priority patent/SE453748B/en
Priority to IT8125614A priority patent/IT1211147B/en
Priority to US06/336,492 priority patent/US4453003A/en
Priority to CA000405157A priority patent/CA1170667A/en
Priority to CA000410051A priority patent/CA1167464A/en
Priority to SE8403931A priority patent/SE466200B/en
Publication of JPS6121466B2 publication Critical patent/JPS6121466B2/ja
Granted legal-status Critical Current

Links

Classifications

    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

PURPOSE: To obtain the title compound, useful as an antiphlogistic agent and an immunity activator, by reducing threo-3-amino-2-hydroxy-4-oxo-4-phenylbutyric acid, etc., and if necessary removing an amino-protecting group or an ester residue, condensing the product with aminoacetic acid, etc.
CONSTITUTION: Compounds of formula II are obtained by the catalytic reduction of threo-3-amino-2-hydroxy-4-oxo-4-phenylbutyric acid or its esters of formula I (R1 is H or OH; R2 is protected amino; R3 is H or an ester residue) with Pd, etc. in a solvent such as acetic acid, at 40W70°C. Subsequently, when the compounds II are (2S,3R)-type compounds, an amino-protecting group is removed if necessary, and an ester residue is removed if it is present, whereby compounds of formula III (R2' is amino or protected amino) are obtained. Then, the compounds III and aminoacetic acid of formula IV (R4 is 3W4C alkyl, etc.) are condensed, protecting a functional group which does not participate in the reaction. After the reaction, the protecting group is removed, to obtain compounds of formula V.
COPYRIGHT: (C)1980,JPO&Japio
JP15315778A 1978-11-25 1978-12-13 Preparation of (2s,3r)-3-amino-2-hydroxy-4- phenylbutanoylaminoacetic acid and its intermediate Granted JPS5579353A (en)

Priority Applications (31)

Application Number Priority Date Filing Date Title
JP15315778A JPS5579353A (en) 1978-12-13 1978-12-13 Preparation of (2s,3r)-3-amino-2-hydroxy-4- phenylbutanoylaminoacetic acid and its intermediate
IT27487/79A IT1194593B (en) 1978-11-25 1979-11-22 PROCEDURE FOR THE PRODUCTION OF TREO-3-AMINO-2-HYDROXYBUTANE-AMINO ACETIC ACIDS AND THEIR INTERMEDIATES
AR278992A AR227636A1 (en) 1978-11-25 1979-11-22 PROCEDURE TO PRODUCE TREO-3-AMINO-2-HYDROXIBUTANOYL AMINOACETIC ACID INTERMEDIARIES TO PREPARE IT AND PROCEDURE TO PREPARE INTERMEDIARIES
ES486572A ES486572A1 (en) 1978-11-25 1979-11-22 Process for producing threo-3-amino-2-hydroxybutanoyl-aminoacetic acids, as well as novel intermediated therefor and process for producing them
FR7928830A FR2442227A1 (en) 1978-11-25 1979-11-22 PROCESS FOR THE PRODUCTION OF THREO-3-AMINO-2-HYDROXYBUTANOYLAMINOACETIC ACIDS
DK496379A DK162288C (en) 1978-11-25 1979-11-22 METHOD FOR PREPARING THREO-3-AMINO-2-HYDROXYBUTANOYL AMINO ACETIC ACIDS
HU79NI230A HU181920B (en) 1978-12-13 1979-11-22 Process for preparing n-threo-/3-amino-2-hydroxy-butanoyl/-amino-acetic acids
GB8200496A GB2090595B (en) 1978-11-25 1979-11-22 Threo-3-amino-2-hydroxybutanoylacetice acid derivatives
CS814806A CS221955B2 (en) 1978-12-13 1979-11-22 Method of making the threo-3-amino-2-hydroxybutane acids
NLAANVRAGE7908510,A NL188162C (en) 1978-11-25 1979-11-22 PROCESS FOR PREPARING A BESTATIN DERIVATIVE.
SE7909655A SE452888B (en) 1978-11-25 1979-11-22 SET TO MAKE TREO-3-AMINO-2-HYDROXIBUTANOYLAMINOETIC ACIDS
DE19792947140 DE2947140A1 (en) 1978-11-25 1979-11-22 PROCESS FOR THE PREPARATION OF THREO-3-AMINO-2-HYDROXYBUTANOYL AMINOACETIC ACID
CS798051A CS221953B2 (en) 1978-12-13 1979-11-22 Method of making the threo-3-amino-2-hydroxybutanoylaminoocto acids
AU53115/79A AU530362B2 (en) 1978-11-25 1979-11-22 Threo-3-amino-2-hydroxy-butanoyl-aminoacetic acids
CH6192/83A CH653669A5 (en) 1978-11-25 1979-11-22 THREO-3-PROTECTED AMINO-2-HYDROXY-4-OXOBUTANIC ACID OR ITS ESTERS AND METHOD FOR THE PRODUCTION THEREOF.
GB7940413A GB2037754B (en) 1978-11-25 1979-11-22 Threo - 3 -protected amino - 2 - hydroxy-4oxobutanoic acids or esters, their preparation and their use in the preparation of threo - 3 - amino - 2 - hydroxy-butanoylaminoacetic acids
DE2954076A DE2954076C2 (en) 1978-11-25 1979-11-22
CH5649/81A CH653687A5 (en) 1978-11-25 1979-11-22 Threo-3-AMINO-2-HYDROXY-BUTANOYLAMINOESSIGSAEURE DERIVATIVES.
CA000340428A CA1182125A (en) 1978-11-25 1979-11-22 Process for producing threo-3-amino-2- hydroxybutanoyl-aminoacetic acids, as well as novel intermediates therefor and process for producing them
CH10433/79A CH650265A5 (en) 1978-11-25 1979-11-22 METHOD FOR THE PRODUCTION OF SUBSTITUTED THREO-3-AMINO-2-HYDROXYBUTANOYLAMINO ACETIC ACIDS.
US06/096,693 US4281180A (en) 1978-11-25 1979-11-23 Process for producing threo-3-amino-2-hydroxybutanoyl-aminoacetic acids, as well as novel intermediated therefor and process for producing them
FR8010563A FR2449078A1 (en) 1978-11-25 1980-05-12 PROCESS FOR THE PRODUCTION OF PROTECTED THREO-3-AMINO ACID 2-HYDROXY-4-OXOBUTANOIC OR ITS ESTERS AND APPLICATION TO THE PRODUCTION OF THREO-3-AMINO-2-HYDROXYBUTANOIC ACID
US06/211,035 US4391986A (en) 1978-11-25 1980-11-28 Process for producing threo-3-amino-2-hydroxybutanoyl-aminoacetic acids, as well as novel intermediates therefor and process for producing them
FR8113611A FR2483409B1 (en) 1978-11-25 1981-07-10 3-AMINO-2-HYDROXY BUTANOYLAMINOACETIC ACID DERIVATIVES AND THEIR PREPARATION PROCESS
NL8104545A NL8104545A (en) 1978-11-25 1981-10-06 "NEW THREO-3-AMINO-2-HYDROXYBUTANOYLAMINO ACETIC ACID DERIVATIVES AND MEDICINES OBTAINED THEREFROM.
SE8106084A SE453748B (en) 1978-11-25 1981-10-14 (2S, 3R) -3-amino-2-hydroxy-4- (4-methoxyphenyl) -BUTANOYL- (S) -leucine
IT8125614A IT1211147B (en) 1978-11-25 1981-12-15 TREO-3-AMINO-2-HYDROXYBUTANE ACIDS NO-ACETIC LAMAGES USEFUL AS DRUGS.
US06/336,492 US4453003A (en) 1978-11-25 1981-12-31 Process for producing threo-3-amino-2-hydroxy-butanoyl-aminoacetic acids as well as novel intermediates therefor and process for producing them
CA000405157A CA1170667A (en) 1978-11-25 1982-06-14 Process for producing threo-3-amino-2-hydroxybutanoyl- aminoacetic acids, as well as novel intermediates therefor and process for producing them
CA000410051A CA1167464A (en) 1978-11-25 1982-08-24 Process for producing threo-3-amino-2-hydroxybutanoyl- aminoacetic acids, as well as novel intermediates therefor and process for producing them
SE8403931A SE466200B (en) 1978-11-25 1984-07-31 TREO-3-PROTECTED AMINO-2-HYDROXY-4-OXO-ACID ACID OR ITS ESTER AND A SEAT FOR PREPARATION THEREOF

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP15315778A JPS5579353A (en) 1978-12-13 1978-12-13 Preparation of (2s,3r)-3-amino-2-hydroxy-4- phenylbutanoylaminoacetic acid and its intermediate

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP26930585A Division JPS61178955A (en) 1985-12-02 1985-12-02 Production of threo-3-amino-2-hydroxy-4-phenylbutyric acid

Publications (2)

Publication Number Publication Date
JPS5579353A true JPS5579353A (en) 1980-06-14
JPS6121466B2 JPS6121466B2 (en) 1986-05-27

Family

ID=15556269

Family Applications (1)

Application Number Title Priority Date Filing Date
JP15315778A Granted JPS5579353A (en) 1978-11-25 1978-12-13 Preparation of (2s,3r)-3-amino-2-hydroxy-4- phenylbutanoylaminoacetic acid and its intermediate

Country Status (3)

Country Link
JP (1) JPS5579353A (en)
CS (2) CS221953B2 (en)
HU (1) HU181920B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009513503A (en) * 2003-07-08 2009-04-02 ユニリーバー・ナームローゼ・ベンノートシヤープ Method for producing cosmetic active ingredients

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009513503A (en) * 2003-07-08 2009-04-02 ユニリーバー・ナームローゼ・ベンノートシヤープ Method for producing cosmetic active ingredients

Also Published As

Publication number Publication date
JPS6121466B2 (en) 1986-05-27
CS221953B2 (en) 1983-04-29
HU181920B (en) 1983-11-28
CS221955B2 (en) 1983-04-29

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