UY24864A1 - Metodo para preparar y purificar un derivado n-alcohilado de aspartamo - Google Patents

Metodo para preparar y purificar un derivado n-alcohilado de aspartamo

Info

Publication number
UY24864A1
UY24864A1 UY24864A UY24864A UY24864A1 UY 24864 A1 UY24864 A1 UY 24864A1 UY 24864 A UY24864 A UY 24864A UY 24864 A UY24864 A UY 24864A UY 24864 A1 UY24864 A1 UY 24864A1
Authority
UY
Uruguay
Prior art keywords
solution
organic solvent
dimethylbutane
aspartyl
phenylalanine
Prior art date
Application number
UY24864A
Other languages
English (en)
Inventor
Prakash Indra
Original Assignee
Nutrasweet Property Holdings Inc
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 Nutrasweet Property Holdings Inc filed Critical Nutrasweet Property Holdings Inc
Publication of UY24864A1 publication Critical patent/UY24864A1/es

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Peptides Or Proteins (AREA)
  • Seasonings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Arrangements For Transmission Of Measured Signals (AREA)
  • Enzymes And Modification Thereof (AREA)

Abstract

Método para purificar 1-metilester de N-[N-(3,3-dimetilbutano)-l-alfa-aspartil]-l-fenilalanina de fórmula general representada en la figura 1, caracterizado porque comprende las etapas de: (1) preparar una solución de 1-metilester de N-[N-(3,3-dimetilbutano)-l-alfa-aspartil]-l-fenilalanina, en un solvente orgánico que se selecciona del grupo formado por metanol, tetrahidrofurano y acetato de etilo; (2) luego formar una solución en agua/solvente orgánico a partir de la solución anterior para precipitar el 1-metilester de N-[N-(3,3-dimetilbutano)-l-alfa-aspartil]-l-fenilalanina desde la solución formada, donde en dicha solución agua/solvente orgánico contiene una cantidad de solvente orgánico de 17% a 30% ponderal de la solución en agua/solvente orgánico. También se incluye el método según lo descrito que incluye un paso previo de tratar un mezcla de aspartamo y 3,3-dimetilbutiraladehído en un solvente orgánico que se selecciona del grupo formado por metanol, tetrahidrofurano y acetato de etilo con hidrógeno en presencia de un catalizador de hidrogenación a una temperatura y a una presión eficaces para formar una solución de 1-metilester de N-[N-(3,3-dimetilbutano)-l-alfa-aspartil]-l-fenilalanina; y luego filtrar dicha solución rn solvente orgánico para sacar el catalizador de hidreogenación. En una realización particular este método se caracteriza porque luego de formarse la solución de agua/solvente orgánico, dicha solución se mantiene por un período de 2 a 4 horas a una temperatura comprendida entre 5 y 25ºC, y/o el pH de la solución en solvente orgánico está comprendido entre 5,0 y 5,5.
UY24864A 1997-01-29 1998-01-29 Metodo para preparar y purificar un derivado n-alcohilado de aspartamo UY24864A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US08/790,113 US5728862A (en) 1997-01-29 1997-01-29 Method for preparing and purifying an N-alkylated aspartame derivative

Publications (1)

Publication Number Publication Date
UY24864A1 true UY24864A1 (es) 1998-02-10

Family

ID=25149681

Family Applications (1)

Application Number Title Priority Date Filing Date
UY24864A UY24864A1 (es) 1997-01-29 1998-01-29 Metodo para preparar y purificar un derivado n-alcohilado de aspartamo

Country Status (29)

Country Link
US (1) US5728862A (es)
EP (1) EP0973796B1 (es)
CN (1) CN1136227C (es)
AR (1) AR011782A1 (es)
AT (1) ATE313555T1 (es)
AU (1) AU723479B2 (es)
BG (1) BG64562B1 (es)
BR (1) BR9807020B1 (es)
CA (1) CA2278608C (es)
CO (1) CO5040054A1 (es)
CZ (1) CZ296888B6 (es)
DE (1) DE69832870T2 (es)
DK (1) DK0973796T3 (es)
EA (1) EA001948B1 (es)
EE (1) EE03928B1 (es)
ES (1) ES2251765T3 (es)
HU (1) HU228676B1 (es)
ID (1) ID22966A (es)
IL (1) IL131140A0 (es)
NO (1) NO326212B1 (es)
NZ (1) NZ336893A (es)
PE (1) PE71999A1 (es)
PL (1) PL191750B1 (es)
SK (1) SK285451B6 (es)
TR (1) TR199901811T2 (es)
TW (1) TW432074B (es)
UA (1) UA57605C2 (es)
UY (1) UY24864A1 (es)
WO (1) WO1998032767A1 (es)

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US6180156B1 (en) 1997-09-11 2001-01-30 The Nutrasweet Company Acid salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester
US6129942A (en) * 1997-09-11 2000-10-10 The Nutrasweet Company Sweetener salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester
US6291004B1 (en) 1997-09-11 2001-09-18 The Nutrasweet Company Basic salts of n-[n-(3,3-dimethylbutyl)-l-α-aspartyl]-l-phenylalanine 1-methyl ester
JPH1180108A (ja) * 1997-09-12 1999-03-26 Ajinomoto Co Inc 甘味料の精製法
JPH11130794A (ja) 1997-10-23 1999-05-18 Ajinomoto Co Inc アスパルテーム誘導体の精製方法
JPH11171895A (ja) * 1997-12-11 1999-06-29 Ajinomoto Co Inc アスパルテームとアスパルテーム誘導体の分離精製方法
JPH11169132A (ja) * 1997-12-15 1999-06-29 Ajinomoto Co Inc アスパルテームとアスパルテーム誘導体の混晶及びその製造方法
US6692778B2 (en) * 1998-06-05 2004-02-17 Wm. Wrigley Jr. Company Method of controlling release of N-substituted derivatives of aspartame in chewing gum
WO1999062354A1 (en) * 1998-06-05 1999-12-09 Wm. Wrigley Jr. Company Method of controlling release of n-substituted derivatives of aspartame in chewing gum and gum produced thereby
US5977415A (en) * 1998-08-20 1999-11-02 The Nutrasweet Company Preparation of 3, 3-dimethylbutyraldehyde from a tert-butyl cation precursor, vinyl chloride and an acidic catalyst
NL1010063C2 (nl) * 1998-09-10 2000-03-13 Holland Sweetener Co Werkwijze voor de bereiding van neotaam.
US6214402B1 (en) 1998-09-17 2001-04-10 The Nutrasweet Company Co-crystallization of sugar and n-[n-(3,3-dimethylbutyl)-l αaspartyl]-l-phenylalanine 1-methyl ester
US5994593A (en) * 1998-09-17 1999-11-30 The Nutrasweet Company Synthesis and purification of 3,3-dimethylbutyraldehyde via hydrolysis of 1,1-dichloro-3,3-dimethylbutane or 1-bromo-1-chloro-3,3-dimethylbutane
US6844465B2 (en) * 1998-10-30 2005-01-18 Ajinomoto Co., Inc. Method for preparing highly stable crystals of aspartame derivative
CN1317012A (zh) 1998-10-30 2001-10-10 味之素株式会社 稳定性优良的天冬甜素衍生物晶体的结晶方法
US6465677B1 (en) 1998-11-19 2002-10-15 The Nutrasweet Company Method for the preparation of N-neohexyl-α-aspartyl-L-phenylalanine methyl ester from imidazolidin-4-one intermediates
WO2000031118A1 (en) * 1998-11-20 2000-06-02 The Nutrasweet Company AMORPHOUS N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
AU1832500A (en) * 1998-11-25 2000-06-19 Nutrasweet Company, The Purification of N-(N-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methyl ester via crystallization
WO2000036933A1 (en) * 1998-12-18 2000-06-29 The Nutrasweet Company USE OF N-NEOHEXYL-α-ASPARTYL-L-PHENYLALANINE METHYL ESTER AS A FLAVOR MODIFIER
US6077962A (en) * 1998-12-24 2000-06-20 The Nutrasweet Company N-3, 3-dimethylbutyl-L-aspartic acid and esters thereof, the process of preparing the same, and the process for preparing N-(N-(3,3-dimethylbutyl) -α L-aspartyl)-L- phenylalanine 1-methyl ester therefrom
US6048999A (en) * 1999-01-25 2000-04-11 The Nutrasweet Company N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester synergistic sweetener blends
US6180157B1 (en) 1999-02-18 2001-01-30 The Nutrasweet Company Process for preparing an N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester agglomerate
AU4449100A (en) * 1999-03-03 2000-09-21 Nutrasweet Company, The Novel crystallization products of neotame and methods for producing same
WO2000057725A1 (en) 1999-03-26 2000-10-05 The Nutrasweet Company PARTICLES OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER
US6573409B1 (en) 1999-07-02 2003-06-03 The Nutrasweet Company Process for the preparation of 3,3-dimethylbutanal
AU4459400A (en) * 1999-07-28 2001-02-19 Nutrasweet Company, The A method for the purification of n-[n-(3,3-dimethylbutyl)-l-alpha-aspartyl]-l-phenylalanine 1-methyl ester
US6506434B1 (en) 1999-08-06 2003-01-14 The Nutrasweet Company Process for coating N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester onto a carrier
KR20020038795A (ko) * 1999-10-07 2002-05-23 에가시라 구니오 아스파르틸디펩타이드 에스테르 유도체의 제조방법과 이를위한 신규한 제조 중간체 및 이의 제조방법
US20040176472A1 (en) * 1999-10-07 2004-09-09 Ajinomoto Co., Inc. Process for production of aspartyl dipeptide ester derivative, novel production intermediate therefor, and process for production thereof
CA2386859A1 (en) * 1999-10-08 2001-04-19 Ajinomoto Co., Inc. Process for production of aspartame derivative, crystal thereof, novel production intermediate therefor, and process for production of intermediate thereof
US6627431B1 (en) * 2000-05-12 2003-09-30 The Nutrasweet Company Chemoenzymatic synthesis of neotame
US6281380B1 (en) * 2000-05-18 2001-08-28 The Nutra Sweet Company Synthesis of N-(N-(3,3-dimethylbutyl)-L-α-aspartyl)L-phenylalanine1-methyl ester by reductive alkylation and crystallization/ isolation in aqueous methanol
DE60115106T2 (de) 2000-05-18 2006-07-13 The Nutrasweet Co., Chicago Herstellung von N-[N-(3,3-Dimethylbutyl)-l-Alpha-Aspartyl]-l-Phenylalanin-1-Methylester durch Verwendung vom l-Alpha-Aspartyl-l-Phenylalanin-1-Methylester als Vorläufer
ATE288446T1 (de) 2000-05-19 2005-02-15 Nutrasweet Co Herstellung von n-(n-(3,3-dimethylbutyl)-l-alpha- aspartyl)- l-phenylalaninmethylester mittels oxazolidinonderivate
US7326430B2 (en) * 2000-07-18 2008-02-05 The Nutrasweet Company Method of preparing liquid compositions for delivery of N-[N- (3,3-dimethylbutyl-L-α-aspartyl]-L-phenylalanine 1-methyl ester in food and beverage systems
US6225493B1 (en) * 2000-08-21 2001-05-01 The Nutrasweet Company Metal ion assisted N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester isomer resolution
AU2001297682A1 (en) * 2000-11-06 2002-09-04 The Nutrasweet Company Catalyst modification to enhance neotame production
US6720446B2 (en) * 2001-11-05 2004-04-13 The Nutrasweet Company Catalyst modification to enhance neotame production
US6782048B2 (en) * 2002-06-21 2004-08-24 Pulse-Link, Inc. Ultra-wideband communication through a wired network
WO2004101604A2 (en) * 2003-05-06 2004-11-25 Nutrasweet Company SYNTHESIS OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER USING 3,3-DIMETHYLBUTYRALDEHYDE PRECURSORS
WO2005087020A1 (en) * 2004-03-05 2005-09-22 Richmond Chemical Corporation High-intensity sweetener-polyol compositions
US20060188629A1 (en) * 2005-01-21 2006-08-24 Greg Liesen Method for the purification of sucralose
CN101270092B (zh) * 2008-04-30 2010-12-08 厦门大学 一种合成纽甜的方法
FR3102041A1 (fr) 2019-10-22 2021-04-23 Aroma Sens Edulcorant pour liquides de cigarette électronique

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JPS59227849A (ja) * 1983-06-08 1984-12-21 Ajinomoto Co Inc Ｌ―α―アスパルチル―Ｌ―フェニルアラニンメチルエステル束状晶の晶析分離法
FR2697844B1 (fr) * 1992-11-12 1995-01-27 Claude Nofre Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation.
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Also Published As

Publication number Publication date
NO326212B1 (no) 2008-10-20
PL191750B1 (pl) 2006-06-30
DE69832870T2 (de) 2006-08-10
DE69832870D1 (de) 2006-01-26
DK0973796T3 (da) 2006-04-18
CN1136227C (zh) 2004-01-28
BR9807020A (pt) 2000-03-14
WO1998032767A1 (en) 1998-07-30
BG103694A (en) 2000-07-31
EA199900690A1 (ru) 2000-04-24
ID22966A (id) 1999-12-23
NO993676L (no) 1999-09-28
PL334882A1 (en) 2000-03-27
HUP0001453A3 (en) 2002-02-28
SK101099A3 (en) 2000-06-12
UA57605C2 (uk) 2003-06-16
CO5040054A1 (es) 2001-05-29
AR011782A1 (es) 2000-09-13
AU6137598A (en) 1998-08-18
IL131140A0 (en) 2001-01-28
AU723479B2 (en) 2000-08-24
EA001948B1 (ru) 2001-10-22
HU228676B1 (en) 2013-05-28
NO993676D0 (no) 1999-07-28
CA2278608C (en) 2002-03-12
CZ261299A3 (cs) 2000-06-14
CZ296888B6 (cs) 2006-07-12
NZ336893A (en) 2001-04-27
HUP0001453A2 (hu) 2000-08-28
US5728862A (en) 1998-03-17
SK285451B6 (sk) 2007-01-04
TR199901811T2 (xx) 1999-12-21
ATE313555T1 (de) 2006-01-15
ES2251765T3 (es) 2006-05-01
BG64562B1 (bg) 2005-07-29
BR9807020B1 (pt) 2011-04-19
EP0973796A1 (en) 2000-01-26
EP0973796B1 (en) 2005-12-21
CN1251107A (zh) 2000-04-19
EE03928B1 (et) 2002-12-16
TW432074B (en) 2001-05-01
CA2278608A1 (en) 1998-07-30
EE9900329A (et) 2000-02-15
PE71999A1 (es) 1999-08-19

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Effective date: 20180129