KR870006084A - N-포르밀-α-L-아스파틸-L-페닐알라닌 메틸 에스테르의 제조방법 - Google Patents
N-포르밀-α-L-아스파틸-L-페닐알라닌 메틸 에스테르의 제조방법 Download PDFInfo
- Publication number
- KR870006084A KR870006084A KR860011117A KR860011117A KR870006084A KR 870006084 A KR870006084 A KR 870006084A KR 860011117 A KR860011117 A KR 860011117A KR 860011117 A KR860011117 A KR 860011117A KR 870006084 A KR870006084 A KR 870006084A
- Authority
- KR
- South Korea
- Prior art keywords
- formyl
- methyl ester
- phenylalanine methyl
- aspartyl
- preparing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 4
- OSEHTEQTVJQGDE-RYUDHWBXSA-N (3s)-3-formamido-4-[[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](NC=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 OSEHTEQTVJQGDE-RYUDHWBXSA-N 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000007810 chemical reaction solvent Substances 0.000 claims 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 235000019253 formic acid Nutrition 0.000 claims 2
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims 1
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 claims 1
- DFTMVZIUYVECNW-VKHMYHEASA-N n-[(3s)-2,5-dioxooxolan-3-yl]formamide Chemical compound O=CN[C@H]1CC(=O)OC1=O DFTMVZIUYVECNW-VKHMYHEASA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
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
-
- 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
Landscapes
- 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)
- Peptides Or Proteins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (3)
- N-포르밀-L-아스파트산무수물과 L-페닐알라닌 메틸 에스테르와의 반응을 아세트산 또는 아세트산과 포름산의 존재하에 반응용매 중에서 완전혼합형 연속반응 방식으로 수행함을 특징으로 하여 N-포르밀-α-L-아스파틸-L-페닐알라닌 메틸에스테르를 제조하는 방법.
- 제1항에 있어서, 반응용매가 톨루엔 또는 에틸 아세테이트인 방법.
- 제1항에 있어서, 존재하는 아세트산 또는 아세트산과 포름산의 양이 반응용매를 기준하여 10 내지 150중량%인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP291180 | 1985-12-24 | ||
JP291180/1985 | 1985-12-24 | ||
JP60291180A JPH0680075B2 (ja) | 1985-12-24 | 1985-12-24 | N―ホルミル―α―L―アスパルチル―L―フェニルアラニンメチルエステルの製造法 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR870006084A true KR870006084A (ko) | 1987-07-09 |
KR930004054B1 KR930004054B1 (ko) | 1993-05-19 |
Family
ID=17765492
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019860011117A KR930004054B1 (ko) | 1985-12-24 | 1986-12-23 | N-포르밀-α-L-아스파틸-L-페닐알라닌 메틸 에스테르의 제조방법 |
Country Status (6)
Country | Link |
---|---|
US (1) | US4820861A (ko) |
EP (1) | EP0227301B1 (ko) |
JP (1) | JPH0680075B2 (ko) |
KR (1) | KR930004054B1 (ko) |
CA (1) | CA1302648C (ko) |
IE (1) | IE59388B1 (ko) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH085912B2 (ja) * | 1986-09-04 | 1996-01-24 | 味の素株式会社 | N−ホルミルアスパルチル−フエニルアラニンまたはそのメチルエステルの製造方法 |
BR9007646A (pt) * | 1988-02-12 | 1992-09-15 | Nutrasweet Co | Processo em recipiente unico de preparacao de hidrocloreto de -apm,processo de copulacao de anidrido n-formil-l-aspartico com l-fenilalanina e processo de preparacao de isomeros de / -n-formil-l-aspartil-l-fenilalanina |
US5053532A (en) * | 1988-02-12 | 1991-10-01 | The Nutra Sweet Company | One-pot process for the preparation of α-L-aspartyl-L-phenylalanine methyl ester hydrochloride |
US4946988A (en) * | 1988-07-14 | 1990-08-07 | The Nutrasweet Company | Process for the preparation of α-L-aspartyl-L-phenylalanine methyl ester hydrochloride by use of isolated N-formyl L-aspartic anhydride |
EP0471833B1 (en) * | 1990-03-12 | 1995-06-14 | The Nutrasweet Company | Method for increasing the alpha to beta ratio in an aspartame coupling reaction |
JP2910228B2 (ja) * | 1990-11-20 | 1999-06-23 | 味の素株式会社 | α―L―アスパルチル―L―フェニルアラニンメチルエステル塩酸塩の製法 |
JP3144430B2 (ja) * | 1991-08-27 | 2001-03-12 | 味の素株式会社 | 有機溶媒の分離方法 |
JPH05178889A (ja) * | 1991-10-30 | 1993-07-20 | Ajinomoto Co Inc | α−L−アスパルチル−L−フェニルアラニンメチルエステルの晶析方法 |
US6657073B1 (en) | 1999-08-18 | 2003-12-02 | Daesang Corporation | Crystallization of α-L-aspartyl-L-phenylalanine methyl ester |
NL1013404C2 (nl) * | 1999-10-27 | 2001-05-01 | Dsm Nv | Werkwijze voor de bereiding van een dipeptide en tussenproduct in een dergelijke werkwijze. |
AU2019415174B2 (en) * | 2018-12-25 | 2022-08-11 | Tokyo Institute Of Technology | Method for producing amide |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3833553A (en) * | 1970-01-31 | 1974-09-03 | Ajinomoto Kk | Method of producing alpha-l-aspartyl-l-phenylalanine alkyl esters |
US3901871A (en) * | 1973-09-21 | 1975-08-26 | American Cyanamid Co | Process of preparing ' -l-aspartyl-l-phenylalanine methyl ester |
US3933781A (en) * | 1973-11-05 | 1976-01-20 | Monsanto Company | Process for the preparation of α-L-aspartyl-L-phenylalanine alkyl esters |
JPS51113841A (en) * | 1975-03-28 | 1976-10-07 | Ajinomoto Co Inc | Process for preparing lower alkyl esters of n-formyl-alpha -l-aspartyl-l-phenylalanine |
JPS5223001A (en) * | 1975-08-14 | 1977-02-21 | Ajinomoto Co Inc | Process for elimination of formyl group |
IE810577L (en) * | 1983-05-31 | 1982-09-16 | Prendergast Angela | Apparatus for fermentation |
US4440677A (en) * | 1983-06-20 | 1984-04-03 | G. D. Searle & Co. | Method and intermediates for producing α-L-aspartyl-L-phenylalanine |
-
1985
- 1985-12-24 JP JP60291180A patent/JPH0680075B2/ja not_active Expired - Fee Related
-
1986
- 1986-11-17 US US06/931,123 patent/US4820861A/en not_active Expired - Lifetime
- 1986-11-19 EP EP86309057A patent/EP0227301B1/en not_active Expired - Lifetime
- 1986-11-21 IE IE308286A patent/IE59388B1/en not_active IP Right Cessation
- 1986-12-02 CA CA000524335A patent/CA1302648C/en not_active Expired - Lifetime
- 1986-12-23 KR KR1019860011117A patent/KR930004054B1/ko not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP0227301A3 (en) | 1989-04-26 |
EP0227301B1 (en) | 1992-05-13 |
IE59388B1 (en) | 1994-02-23 |
JPS62149699A (ja) | 1987-07-03 |
JPH0680075B2 (ja) | 1994-10-12 |
IE863082L (en) | 1987-06-24 |
CA1302648C (en) | 1992-06-02 |
KR930004054B1 (ko) | 1993-05-19 |
EP0227301A2 (en) | 1987-07-01 |
US4820861A (en) | 1989-04-11 |
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