JPS6112919B2 - - Google Patents
Info
- Publication number
- JPS6112919B2 JPS6112919B2 JP7608279A JP7608279A JPS6112919B2 JP S6112919 B2 JPS6112919 B2 JP S6112919B2 JP 7608279 A JP7608279 A JP 7608279A JP 7608279 A JP7608279 A JP 7608279A JP S6112919 B2 JPS6112919 B2 JP S6112919B2
- Authority
- JP
- Japan
- Prior art keywords
- aspartyl
- lower alkyl
- alkyl ester
- aqueous medium
- crystals
- 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.)
- Expired
Links
- 125000005907 alkyl ester group Chemical group 0.000 claims description 36
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 claims description 30
- 239000012736 aqueous medium Substances 0.000 claims description 28
- 239000013078 crystal Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 15
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical group OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000356 contaminant Substances 0.000 claims description 2
- XYXLNYSVQVWRQL-UHFFFAOYSA-N 2-(2,5-dioxopiperazin-1-yl)acetic acid Chemical compound OC(=O)CN1CC(=O)NCC1=O XYXLNYSVQVWRQL-UHFFFAOYSA-N 0.000 claims 2
- LDHLAFGSAQPXBS-UHFFFAOYSA-N 2-(1-benzyl-3,6-dioxopiperazin-2-yl)acetic acid Chemical compound O=C1CNC(=O)C(CC(=O)O)N1CC1=CC=CC=C1 LDHLAFGSAQPXBS-UHFFFAOYSA-N 0.000 claims 1
- STTIAONCINEOLF-UHFFFAOYSA-N 2-(3,6-dioxopiperazin-2-yl)acetic acid Chemical compound OC(=O)CC1NC(=O)CNC1=O STTIAONCINEOLF-UHFFFAOYSA-N 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229960005190 phenylalanine Drugs 0.000 description 5
- 238000005259 measurement Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- VNHJXYUDIBQDDX-UHFFFAOYSA-N L-cis-Cyclo(aspartylphenylalanyl) Chemical compound N1C(=O)C(CC(=O)O)NC(=O)C1CC1=CC=CC=C1 VNHJXYUDIBQDDX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7608279A JPS55167268A (en) | 1979-06-16 | 1979-06-16 | Purification of alpha-l-aspartyl-l-phenylalanine lower alkyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7608279A JPS55167268A (en) | 1979-06-16 | 1979-06-16 | Purification of alpha-l-aspartyl-l-phenylalanine lower alkyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55167268A JPS55167268A (en) | 1980-12-26 |
| JPS6112919B2 true JPS6112919B2 (ru) | 1986-04-10 |
Family
ID=13594894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7608279A Granted JPS55167268A (en) | 1979-06-16 | 1979-06-16 | Purification of alpha-l-aspartyl-l-phenylalanine lower alkyl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55167268A (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58177952A (ja) * | 1982-04-12 | 1983-10-18 | Ajinomoto Co Inc | Ｌ−α−アスパルチル−Ｌ−フエニルアラニンメチルエステルの晶析法 |
| DE3635582A1 (de) * | 1986-10-20 | 1988-04-21 | Hoechst Ag | Verfahren zur reinigung von n-acyl-aspartam |
| JPH05500371A (ja) * | 1988-02-12 | 1993-01-28 | ザ ヌトラスウィート カンパニー | α―Ｌ―アルパルチル―Ｌ―フェニルアラニンメチルエステル塩酸塩のワンポット製造法 |
-
1979
- 1979-06-16 JP JP7608279A patent/JPS55167268A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55167268A (en) | 1980-12-26 |
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