JPS6034955A - ２−オキソオキサゾリジン−４−カルボン酸類の製造法 - Google Patents
２−オキソオキサゾリジン−４−カルボン酸類の製造法Info
- Publication number
- JPS6034955A JPS6034955A JP14247583A JP14247583A JPS6034955A JP S6034955 A JPS6034955 A JP S6034955A JP 14247583 A JP14247583 A JP 14247583A JP 14247583 A JP14247583 A JP 14247583A JP S6034955 A JPS6034955 A JP S6034955A
- Authority
- JP
- Japan
- Prior art keywords
- carbonate
- bicarbonate
- water
- amino
- acid
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- XMFFFMBLTDERID-UHFFFAOYSA-N 2-oxo-1,3-oxazolidine-4-carboxylic acid Chemical class OC(=O)C1COC(=O)N1 XMFFFMBLTDERID-UHFFFAOYSA-N 0.000 title description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 6
- -1 etc. Inorganic materials 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001340 alkali metals Chemical class 0.000 abstract description 4
- 239000003125 aqueous solvent Substances 0.000 abstract description 4
- 235000008206 alpha-amino acids Nutrition 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 abstract description 2
- 229910052791 calcium Inorganic materials 0.000 abstract description 2
- 229910052744 lithium Inorganic materials 0.000 abstract description 2
- 229910052749 magnesium Inorganic materials 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 229910052700 potassium Inorganic materials 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- ASBJGPTTYPEMLP-UHFFFAOYSA-N 3-chloroalanine Chemical compound ClCC(N)C(O)=O ASBJGPTTYPEMLP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 150000007513 acids Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ORQLXCMGAMWKMJ-REOHCLBHSA-N (2r)-2-amino-3-bromopropanoic acid Chemical compound BrC[C@H](N)C(O)=O ORQLXCMGAMWKMJ-REOHCLBHSA-N 0.000 description 1
- IENJPSDBNBGIEL-DKWTVANSSA-N (2r)-2-amino-3-chloropropanoic acid;hydrochloride Chemical compound Cl.ClC[C@H](N)C(O)=O IENJPSDBNBGIEL-DKWTVANSSA-N 0.000 description 1
- YFYASMWDAMXQQT-UHFFFAOYSA-N 2-amino-3-chlorobutanoic acid Chemical compound CC(Cl)C(N)C(O)=O YFYASMWDAMXQQT-UHFFFAOYSA-N 0.000 description 1
- KYNKAUUXUQOZSQ-UHFFFAOYSA-N 5-methyl-2-oxo-1,3-oxazolidine-4-carboxylic acid Chemical compound CC1OC(=O)NC1C(O)=O KYNKAUUXUQOZSQ-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000981595 Zoysia japonica Species 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000004653 carbonic acids Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- POPBCSXDEXRDSX-DFWYDOINSA-N methyl (2r)-2-amino-3-chloropropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CCl POPBCSXDEXRDSX-DFWYDOINSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14247583A JPS6034955A (ja) | 1983-08-05 | 1983-08-05 | ２−オキソオキサゾリジン−４−カルボン酸類の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14247583A JPS6034955A (ja) | 1983-08-05 | 1983-08-05 | ２−オキソオキサゾリジン−４−カルボン酸類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6034955A true JPS6034955A (ja) | 1985-02-22 |
| JPH0449547B2 JPH0449547B2 (en, 2012) | 1992-08-11 |
Family
ID=15316179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14247583A Granted JPS6034955A (ja) | 1983-08-05 | 1983-08-05 | ２−オキソオキサゾリジン−４−カルボン酸類の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6034955A (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0844233A1 (en) * | 1996-11-26 | 1998-05-27 | Dsm N.V. | Process for preparing alpha-amino acid amides, alpha-amino acids and derivatives thereof |
| WO1999002508A1 (fr) * | 1997-07-10 | 1999-01-21 | Ube Industries, Ltd. | Procede de preparation de composes de 4-alcoxycarbonyl-2-oxazolidinone |
| US6541641B1 (en) | 1999-08-30 | 2003-04-01 | Shionogi & Co., Ltd. | Processes for the preparation of oxo-oxazoline or alloamino acid derivatives |
-
1983
- 1983-08-05 JP JP14247583A patent/JPS6034955A/ja active Granted
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0844233A1 (en) * | 1996-11-26 | 1998-05-27 | Dsm N.V. | Process for preparing alpha-amino acid amides, alpha-amino acids and derivatives thereof |
| BE1010768A3 (nl) * | 1996-11-26 | 1999-01-05 | Dsm Nv | Een werkwijze voor de bereiding van alpha-aminozuuramiden, alpha-aminozuren en derivaten ervan. |
| WO1999002508A1 (fr) * | 1997-07-10 | 1999-01-21 | Ube Industries, Ltd. | Procede de preparation de composes de 4-alcoxycarbonyl-2-oxazolidinone |
| US6414160B1 (en) * | 1997-07-10 | 2002-07-02 | Ube Industries, Ltd. | Process for producing 4-alkoxycarbonyl-2-oxazolidinone compound |
| US6541641B1 (en) | 1999-08-30 | 2003-04-01 | Shionogi & Co., Ltd. | Processes for the preparation of oxo-oxazoline or alloamino acid derivatives |
| US6747157B2 (en) | 1999-08-30 | 2004-06-08 | Shionogi & Co., Ltd. | Processes for the preparation of oxo-oxazoline or alloamino acid derivatives |
| US6875874B2 (en) | 1999-08-30 | 2005-04-05 | Shionogi & Co., Ltd. | Processes for the preparation of oxo-oxazoline or alloamino acid derivatives |
| US7189857B2 (en) | 1999-08-30 | 2007-03-13 | Shionogi & Co., Ltd. | Processes for the preparation of oxo-oxazoline or alloamino acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0449547B2 (en, 2012) | 1992-08-11 |
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