DE2134251C3 - Verfahren zur Herstellung von 4-Hydroxyphenyl-glycin - Google Patents
Verfahren zur Herstellung von 4-Hydroxyphenyl-glycinInfo
- Publication number
- DE2134251C3 DE2134251C3 DE2134251A DE2134251A DE2134251C3 DE 2134251 C3 DE2134251 C3 DE 2134251C3 DE 2134251 A DE2134251 A DE 2134251A DE 2134251 A DE2134251 A DE 2134251A DE 2134251 C3 DE2134251 C3 DE 2134251C3
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- ammonia
- reaction
- glyoxylic acid
- glycine
- 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 16
- 238000002360 preparation method Methods 0.000 title claims 2
- LJCWONGJFPCTTL-ZETCQYMHSA-N L-4-hydroxyphenylglycine Chemical compound OC(=O)[C@@H](N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-ZETCQYMHSA-N 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 43
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 36
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 13
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 11
- LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 claims description 11
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 238000012619 stoichiometric conversion Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZHIBZCPDMCUVRA-UHFFFAOYSA-N 2-amino-2-(4-hydroxyphenyl)acetic acid;hydrochloride Chemical compound Cl.OC(=O)C(N)C1=CC=C(O)C=C1 ZHIBZCPDMCUVRA-UHFFFAOYSA-N 0.000 description 2
- HIQIUINFXZKKEC-UHFFFAOYSA-N 2-anilinoacetic acid;hydrochloride Chemical compound Cl.OC(=O)CNC1=CC=CC=C1 HIQIUINFXZKKEC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- -1 camphor sulfone Chemical class 0.000 description 2
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 2
- 229960002449 glycine Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- QDAYZTZGLPEDOB-UHFFFAOYSA-N 2-(2-hydroxyanilino)acetic acid Chemical class OC(=O)CNC1=CC=CC=C1O QDAYZTZGLPEDOB-UHFFFAOYSA-N 0.000 description 1
- ALCYPYQGMTVEKV-UHFFFAOYSA-N 2-(4-hydroxyanilino)acetic acid;hydrochloride Chemical compound Cl.OC(=O)CNC1=CC=C(O)C=C1 ALCYPYQGMTVEKV-UHFFFAOYSA-N 0.000 description 1
- KKLMJYDGZSAIQX-UHFFFAOYSA-N 2-(n-hydroxyanilino)acetic acid Chemical compound OC(=O)CN(O)C1=CC=CC=C1 KKLMJYDGZSAIQX-UHFFFAOYSA-N 0.000 description 1
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 241000243127 Geodia Species 0.000 description 1
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- IYSKBOAWMYJGBG-UHFFFAOYSA-N azanium;oxaldehydate Chemical compound [NH4+].[O-]C(=O)C=O IYSKBOAWMYJGBG-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960001269 glycine hydrochloride Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/12—Formation of amino and carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
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 |
|---|---|---|---|
| GB3378970 | 1970-07-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2134251A1 DE2134251A1 (de) | 1972-01-27 |
| DE2134251B2 DE2134251B2 (de) | 1973-09-06 |
| DE2134251C3 true DE2134251C3 (de) | 1974-04-18 |
Family
ID=10357462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2134251A Expired DE2134251C3 (de) | 1970-07-11 | 1971-07-09 | Verfahren zur Herstellung von 4-Hydroxyphenyl-glycin |
Country Status (12)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5917104B2 (ja) * | 1977-05-02 | 1984-04-19 | 田辺製薬株式会社 | ヒドロキシフエニルグリシン類化合物の製法 |
| GB1576334A (en) * | 1977-05-26 | 1980-10-08 | Ici Ltd | N-alkyl and n,n-dialkyl derivatives thereof process for the manufacture of p-hydroxyphenylglycine and |
| EP0001319A1 (en) * | 1977-08-18 | 1979-04-04 | Beecham Group Plc | Process for the preparation of hydroxyphenyl hydantoin and of hydroxyphenyl glycine, and compounds thus obtained |
-
1970
- 1970-07-11 GB GB3378970A patent/GB1353612A/en not_active Expired
-
1971
- 1971-07-05 IL IL37237A patent/IL37237A/xx unknown
- 1971-07-07 FI FI1913/71A patent/FI53451C/fi active
- 1971-07-08 BE BE769708A patent/BE769708A/xx not_active IP Right Cessation
- 1971-07-08 FR FR7125034A patent/FR2100416A5/fr not_active Expired
- 1971-07-09 DE DE2134251A patent/DE2134251C3/de not_active Expired
- 1971-07-09 SE SE7108917A patent/SE394669B/xx unknown
- 1971-07-09 AT AT600871A patent/AT314506B/de not_active IP Right Cessation
- 1971-07-09 NL NL717109511A patent/NL148590B/xx not_active IP Right Cessation
- 1971-07-09 DK DK338671AA patent/DK137324B/da not_active IP Right Cessation
- 1971-07-10 JP JP5138671A patent/JPS5343950B1/ja active Pending
- 1971-07-10 CH CH1017471A patent/CH559165A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1353612A (en) | 1974-05-22 |
| IL37237A (en) | 1975-04-25 |
| SE394669B (sv) | 1977-07-04 |
| AT314506B (de) | 1974-04-10 |
| DK137324B (da) | 1978-02-20 |
| DK137324C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-07-17 |
| BE769708A (fr) | 1971-11-16 |
| DE2134251B2 (de) | 1973-09-06 |
| CH559165A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-28 |
| DE2134251A1 (de) | 1972-01-27 |
| IL37237A0 (en) | 1971-10-20 |
| FI53451C (fi) | 1978-05-10 |
| NL148590B (nl) | 1976-02-16 |
| FI53451B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-01-31 |
| JPS5343950B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-11-24 |
| NL7109511A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-01-13 |
| FR2100416A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |