DE2605567C3 - Verfahren zur Gewinnung von optisch aktivem a Phenylglycin-hydrochlorid - Google Patents
Verfahren zur Gewinnung von optisch aktivem a Phenylglycin-hydrochloridInfo
- Publication number
- DE2605567C3 DE2605567C3 DE19762605567 DE2605567A DE2605567C3 DE 2605567 C3 DE2605567 C3 DE 2605567C3 DE 19762605567 DE19762605567 DE 19762605567 DE 2605567 A DE2605567 A DE 2605567A DE 2605567 C3 DE2605567 C3 DE 2605567C3
- Authority
- DE
- Germany
- Prior art keywords
- phenylglycine
- hydrochloride
- solution
- optically active
- phenylglycine hydrochloride
- 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
- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- HIQIUINFXZKKEC-UHFFFAOYSA-N 2-anilinoacetic acid;hydrochloride Chemical compound Cl.OC(=O)CNC1=CC=CC=C1 HIQIUINFXZKKEC-UHFFFAOYSA-N 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 44
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000012043 crude product Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000011592 zinc chloride Substances 0.000 claims description 10
- 235000005074 zinc chloride Nutrition 0.000 claims description 10
- IAZPUJDTYUZJMI-UHFFFAOYSA-N [carboxy(phenyl)methyl]azanium;chloride Chemical compound Cl.OC(=O)C(N)C1=CC=CC=C1 IAZPUJDTYUZJMI-UHFFFAOYSA-N 0.000 claims description 8
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 claims description 6
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 5
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 235000011150 stannous chloride Nutrition 0.000 claims description 5
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 5
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 3
- 229910052742 iron Inorganic materials 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 41
- 239000013078 crystal Substances 0.000 description 17
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 14
- 230000003287 optical effect Effects 0.000 description 14
- 238000000926 separation method Methods 0.000 description 12
- 229910001510 metal chloride Inorganic materials 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- IAZPUJDTYUZJMI-OGFXRTJISA-N (2r)-2-amino-2-phenylacetic acid;hydrochloride Chemical compound Cl.OC(=O)[C@H](N)C1=CC=CC=C1 IAZPUJDTYUZJMI-OGFXRTJISA-N 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 238000001640 fractional crystallisation Methods 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 238000010956 selective crystallization Methods 0.000 description 4
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IAZPUJDTYUZJMI-FJXQXJEOSA-N (2s)-2-amino-2-phenylacetic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)C1=CC=CC=C1 IAZPUJDTYUZJMI-FJXQXJEOSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 101150050048 SNCB gene Proteins 0.000 description 1
- 229910008433 SnCU Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50023072A JPS5198237A (en) | 1975-02-25 | 1975-02-25 | Kogakukatsusei aa fuenirugurishinensanenno seizoho |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2605567A1 DE2605567A1 (de) | 1976-09-02 |
| DE2605567B2 DE2605567B2 (de) | 1977-11-24 |
| DE2605567C3 true DE2605567C3 (de) | 1978-08-03 |
Family
ID=12100185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762605567 Expired DE2605567C3 (de) | 1975-02-25 | 1976-02-12 | Verfahren zur Gewinnung von optisch aktivem a Phenylglycin-hydrochlorid |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5198237A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2605567C3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2302288A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1478450A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1055945B (cg-RX-API-DMAC7.html) |
| NL (1) | NL162630C (cg-RX-API-DMAC7.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105795B (zh) * | 2022-01-28 | 2022-04-08 | 天津市职业大学 | 一种阿莫西林生产中间体的合成方法 |
-
1975
- 1975-02-25 JP JP50023072A patent/JPS5198237A/ja active Granted
-
1976
- 1976-02-12 DE DE19762605567 patent/DE2605567C3/de not_active Expired
- 1976-02-18 GB GB646276A patent/GB1478450A/en not_active Expired
- 1976-02-19 NL NL7601674A patent/NL162630C/xx not_active IP Right Cessation
- 1976-02-24 FR FR7605128A patent/FR2302288A1/fr active Granted
- 1976-02-25 IT IT2057876A patent/IT1055945B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2302288A1 (fr) | 1976-09-24 |
| IT1055945B (it) | 1982-01-11 |
| NL162630C (nl) | 1980-06-16 |
| DE2605567A1 (de) | 1976-09-02 |
| JPS568828B2 (cg-RX-API-DMAC7.html) | 1981-02-25 |
| NL162630B (nl) | 1980-01-15 |
| GB1478450A (en) | 1977-06-29 |
| FR2302288B1 (cg-RX-API-DMAC7.html) | 1979-04-20 |
| DE2605567B2 (de) | 1977-11-24 |
| JPS5198237A (en) | 1976-08-30 |
| NL7601674A (nl) | 1976-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |