NL192112C - Werkwijze voor de bereiding van aspartaam. - Google Patents
Werkwijze voor de bereiding van aspartaam. Download PDFInfo
- Publication number
- NL192112C NL192112C NL8401674A NL8401674A NL192112C NL 192112 C NL192112 C NL 192112C NL 8401674 A NL8401674 A NL 8401674A NL 8401674 A NL8401674 A NL 8401674A NL 192112 C NL192112 C NL 192112C
- Authority
- NL
- Netherlands
- Prior art keywords
- methyl ester
- aspartyl
- phenylalanine methyl
- phosphoric acid
- phosphate
- Prior art date
Links
- 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 title claims description 17
- 238000000034 method Methods 0.000 title claims description 15
- 108010011485 Aspartame Proteins 0.000 title claims description 11
- 239000000605 aspartame Substances 0.000 title claims description 11
- 229960003438 aspartame Drugs 0.000 title claims description 11
- 235000010357 aspartame Nutrition 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 12
- 239000010452 phosphate Substances 0.000 claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 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 claims description 6
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 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 description 2
- 229960005190 phenylalanine Drugs 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000009413 insulation Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 2
- 108010016626 Dipeptides Proteins 0.000 description 1
- CZMRCDWAGMRECN-UHFFFAOYSA-N Rohrzucker Natural products OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000006344 deformylation reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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)
- Seasonings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8314907 | 1983-05-31 | ||
| GB838314907A GB8314907D0 (en) | 1983-05-31 | 1983-05-31 | Aspartame synthesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL8401674A NL8401674A (nl) | 1984-12-17 |
| NL192112B NL192112B (nl) | 1996-10-01 |
| NL192112C true NL192112C (nl) | 1997-02-04 |
Family
ID=10543585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8401674A NL192112C (nl) | 1983-05-31 | 1984-05-25 | Werkwijze voor de bereiding van aspartaam. |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4656304A (en, 2012) |
| JP (1) | JPS59227850A (en, 2012) |
| KR (1) | KR910002387B1 (en, 2012) |
| AT (1) | AT387024B (en, 2012) |
| AU (1) | AU561593B2 (en, 2012) |
| BE (1) | BE899783A (en, 2012) |
| CA (1) | CA1244008A (en, 2012) |
| CH (1) | CH659061A5 (en, 2012) |
| CS (1) | CS257778B2 (en, 2012) |
| DE (1) | DE3419921A1 (en, 2012) |
| DK (1) | DK163928C (en, 2012) |
| ES (1) | ES8506598A1 (en, 2012) |
| FI (1) | FI80465C (en, 2012) |
| FR (1) | FR2547816B1 (en, 2012) |
| GB (1) | GB8314907D0 (en, 2012) |
| GR (1) | GR82034B (en, 2012) |
| HU (1) | HU191146B (en, 2012) |
| IE (2) | IE810577L (en, 2012) |
| IL (1) | IL71930A (en, 2012) |
| IT (1) | IT1212097B (en, 2012) |
| NL (1) | NL192112C (en, 2012) |
| NO (1) | NO163738C (en, 2012) |
| NZ (1) | NZ208279A (en, 2012) |
| PH (1) | PH21764A (en, 2012) |
| PT (1) | PT78657B (en, 2012) |
| SE (1) | SE459176B (en, 2012) |
| SU (1) | SU1342423A3 (en, 2012) |
| YU (1) | YU44456B (en, 2012) |
| ZA (1) | ZA844071B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0680075B2 (ja) * | 1985-12-24 | 1994-10-12 | 味の素株式会社 | 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 |
| US5283357A (en) * | 1988-03-14 | 1994-02-01 | Mitsui Toatsu Chemicals, Incorporated | Separation method of α-l-aspartyl-l-phenylalanine methyl ester |
| JP2662287B2 (ja) * | 1988-03-14 | 1997-10-08 | 三井東圧化学株式会社 | α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルの分離方法 |
| US5017690A (en) * | 1989-08-11 | 1991-05-21 | W. R. Grace & Co.-Conn. | Deblocking N-formyl aspartame compounds |
| NL9201408A (nl) * | 1992-08-05 | 1994-03-01 | Holland Sweetener Co | Werkwijze voor het kristalliseren van aspartaam. |
| BE1010071A3 (nl) * | 1996-04-10 | 1997-12-02 | Holland Sweetener Co | Aspartaam op drager. |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3492131A (en) * | 1966-04-18 | 1970-01-27 | Searle & Co | Peptide sweetening agents |
| US3833553A (en) * | 1970-01-31 | 1974-09-03 | Ajinomoto Kk | Method of producing alpha-l-aspartyl-l-phenylalanine alkyl esters |
| JPS5140069B1 (en, 2012) * | 1971-07-09 | 1976-11-01 | ||
| BE791544A (fr) * | 1971-11-19 | 1973-05-17 | Stamicarbon | Preparation d'esters alkyliques de dipeptide |
| JPS5113737A (en) * | 1974-07-23 | 1976-02-03 | Ajinomoto Kk | Arufua ll asuparuchiru ll fueniruaraninteikyuarukiruesuteruno seizoho |
| JPS5223001A (en) * | 1975-08-14 | 1977-02-21 | Ajinomoto Co Inc | Process for elimination of formyl group |
| US4173562A (en) * | 1976-12-27 | 1979-11-06 | Monsanto Company | Process for the preparation of α-L-aspartyl-L-phenylalanine methyl ester |
| JPS57131746A (en) * | 1981-02-10 | 1982-08-14 | Ajinomoto Co Inc | Removal of n-formyl group |
| JPS58185545A (ja) * | 1982-04-22 | 1983-10-29 | Ajinomoto Co Inc | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルまたはその塩酸塩の製法 |
-
1981
- 1981-03-16 IE IE810577A patent/IE810577L/xx unknown
-
1983
- 1983-05-31 GB GB838314907A patent/GB8314907D0/en active Pending
-
1984
- 1984-05-15 FI FI841952A patent/FI80465C/fi not_active IP Right Cessation
- 1984-05-24 GR GR74819A patent/GR82034B/el unknown
- 1984-05-24 FR FR8408119A patent/FR2547816B1/fr not_active Expired
- 1984-05-24 AT AT0172384A patent/AT387024B/de not_active IP Right Cessation
- 1984-05-25 NZ NZ208279A patent/NZ208279A/en unknown
- 1984-05-25 IL IL71930A patent/IL71930A/xx unknown
- 1984-05-25 IE IE1312/84A patent/IE57662B1/en not_active IP Right Cessation
- 1984-05-25 CA CA000455169A patent/CA1244008A/en not_active Expired
- 1984-05-25 US US06/614,150 patent/US4656304A/en not_active Expired - Fee Related
- 1984-05-25 NL NL8401674A patent/NL192112C/nl not_active IP Right Cessation
- 1984-05-25 SU SU843743902A patent/SU1342423A3/ru active
- 1984-05-28 DE DE3419921A patent/DE3419921A1/de active Granted
- 1984-05-28 CS CS843998A patent/CS257778B2/cs unknown
- 1984-05-28 PT PT78657A patent/PT78657B/pt not_active IP Right Cessation
- 1984-05-28 HU HU842057A patent/HU191146B/hu not_active IP Right Cessation
- 1984-05-28 AU AU28767/84A patent/AU561593B2/en not_active Ceased
- 1984-05-29 ES ES532916A patent/ES8506598A1/es not_active Expired
- 1984-05-29 IT IT8421147A patent/IT1212097B/it active
- 1984-05-29 NO NO842129A patent/NO163738C/no unknown
- 1984-05-29 ZA ZA844071A patent/ZA844071B/xx unknown
- 1984-05-29 CH CH2630/84A patent/CH659061A5/it not_active IP Right Cessation
- 1984-05-29 JP JP59107667A patent/JPS59227850A/ja active Granted
- 1984-05-29 BE BE0/213030A patent/BE899783A/fr not_active IP Right Cessation
- 1984-05-29 PH PH30733A patent/PH21764A/en unknown
- 1984-05-30 KR KR1019840002999A patent/KR910002387B1/ko not_active Expired
- 1984-05-30 DK DK270084A patent/DK163928C/da not_active IP Right Cessation
- 1984-05-30 YU YU922/84A patent/YU44456B/xx unknown
- 1984-05-30 SE SE8402953A patent/SE459176B/sv not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4173562A (en) | Process for the preparation of α-L-aspartyl-L-phenylalanine methyl ester | |
| NL192112C (nl) | Werkwijze voor de bereiding van aspartaam. | |
| HU179735B (en) | Improved process for producing alpha-l-asparagyl-phenyl-alanine methyl-esters | |
| US4348317A (en) | Recovery of L-phenylalanine and L-aspartic acid during preparation of α-L-aspartyl-L-phenylalanine methyl ester | |
| GB2140805A (en) | Isolation of aspartame | |
| GB2144748A (en) | Aspartame synthesis | |
| IE52264B1 (en) | Process for removing an n-formyl group | |
| JP3208874B2 (ja) | α−Ｌ−アスパルチル−Ｌ−フェニルアラニンの製造法 | |
| EP0514938B1 (en) | Method of preparing alpha-L-aspartyl-L-phenylalanine methyl ester hydrochloride | |
| EP0986575B1 (en) | Method for preparing salts of aspartame from n-protected aspartame | |
| CA1322626C (en) | Process for the preparation of aspartylphenylalanine methyl ester from n-formylaspartylphenylalanine methyl ester | |
| EP0581032B1 (en) | Method for production of alpha-L-aspartyl-L-phenylalanine methyl ester hydrochloride | |
| EP0169937A2 (en) | Process for the preparation of alpha-L-aspartyl-L-phenylalanine alkyl esters | |
| JP3316910B2 (ja) | Ｌ−フェニルアラニンの回収方法 | |
| JPH0730049B2 (ja) | ジケトピペラジン誘導体の製造方法 | |
| JPS63141993A (ja) | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルのハロゲン化水素酸塩の製造方法 | |
| JPS61197592A (ja) | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BK | Erratum |
Free format text: PAT.BUL.04/97,HEADING P,SECTION 2 PAGE 494:THE TITLE OF THE INVENTION SHOULD READ:WERKWIJZE VOOR DEBEREIDING VAN DE A-L-ASPARTYL-L-FENYLALANINE-METHYLESTER |
|
| V1 | Lapsed because of non-payment of the annual fee |
Effective date: 19971201 |