IE51920B1 - Preparation of l-aspartic acid n-thicocarboxyanhydride - Google Patents
Preparation of l-aspartic acid n-thicocarboxyanhydrideInfo
- Publication number
- IE51920B1 IE51920B1 IE2588/81A IE258881A IE51920B1 IE 51920 B1 IE51920 B1 IE 51920B1 IE 2588/81 A IE2588/81 A IE 2588/81A IE 258881 A IE258881 A IE 258881A IE 51920 B1 IE51920 B1 IE 51920B1
- Authority
- IE
- Ireland
- Prior art keywords
- process according
- thiocarboxyanhydride
- aspartic acid
- aspartic
- salt
- Prior art date
Links
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 title claims abstract description 24
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 title claims abstract description 24
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title claims abstract description 24
- 229960005261 aspartic acid Drugs 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims description 7
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- GWKOSRIHVSBBIA-REOHCLBHSA-N (3s)-3-aminooxolane-2,5-dione Chemical compound N[C@H]1CC(=O)OC1=O GWKOSRIHVSBBIA-REOHCLBHSA-N 0.000 claims abstract description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000012429 reaction media Substances 0.000 claims description 10
- -1 alkyl acetate Chemical compound 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 125000005270 trialkylamine group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 7
- ZUOVTYLEICKQDF-DKWTVANSSA-N (3s)-3-aminooxolane-2,5-dione;hydrochloride Chemical compound Cl.N[C@H]1CC(=O)OC1=O ZUOVTYLEICKQDF-DKWTVANSSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 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 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000012430 organic reaction media Substances 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/204,135 US4321391A (en) | 1980-11-05 | 1980-11-05 | Preparation of L-aspartic acid N-thiocarboxyanhydride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE812588L IE812588L (en) | 1982-05-05 |
| IE51920B1 true IE51920B1 (en) | 1987-04-29 |
Family
ID=22756779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2588/81A IE51920B1 (en) | 1980-11-05 | 1981-11-04 | Preparation of l-aspartic acid n-thicocarboxyanhydride |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4321391A (en:Method) |
| EP (1) | EP0051956B1 (en:Method) |
| JP (1) | JPS6036434B2 (en:Method) |
| DE (1) | DE3169435D1 (en:Method) |
| DK (1) | DK153146C (en:Method) |
| GR (1) | GR76295B (en:Method) |
| IE (1) | IE51920B1 (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102013201589A1 (de) | 2013-01-31 | 2014-07-31 | BSH Bosch und Siemens Hausgeräte GmbH | Kältegerät mit einem Behälter |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846398A (en) * | 1969-04-17 | 1974-11-05 | Merck & Co Inc | Method for controlled stepwise synthesis of polypeptides utilizing n-thiocarboxy anhydrides of amino acids as reagents |
| US4256897A (en) * | 1979-10-29 | 1981-03-17 | Pfizer Inc. | Process for the preparation of L-aspartic acid N-thiocarboxyanhydride |
-
1980
- 1980-11-05 US US06/204,135 patent/US4321391A/en not_active Expired - Lifetime
-
1981
- 1981-10-27 EP EP81305056A patent/EP0051956B1/en not_active Expired
- 1981-10-27 DE DE8181305056T patent/DE3169435D1/de not_active Expired
- 1981-11-03 GR GR66420A patent/GR76295B/el unknown
- 1981-11-04 JP JP56177016A patent/JPS6036434B2/ja not_active Expired
- 1981-11-04 IE IE2588/81A patent/IE51920B1/en not_active IP Right Cessation
- 1981-11-04 DK DK487981A patent/DK153146C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK153146B (da) | 1988-06-20 |
| DK153146C (da) | 1988-10-24 |
| DK487981A (da) | 1982-05-06 |
| JPS6036434B2 (ja) | 1985-08-20 |
| JPS57108084A (en) | 1982-07-05 |
| US4321391A (en) | 1982-03-23 |
| DE3169435D1 (en) | 1985-04-25 |
| EP0051956A1 (en) | 1982-05-19 |
| EP0051956B1 (en) | 1985-03-20 |
| GR76295B (en:Method) | 1984-08-04 |
| IE812588L (en) | 1982-05-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |