IE41879B1 - Process for optical purification of d-p-hydroxyphenylglycine - Google Patents
Process for optical purification of d-p-hydroxyphenylglycineInfo
- Publication number
- IE41879B1 IE41879B1 IE2458/75A IE245875A IE41879B1 IE 41879 B1 IE41879 B1 IE 41879B1 IE 2458/75 A IE2458/75 A IE 2458/75A IE 245875 A IE245875 A IE 245875A IE 41879 B1 IE41879 B1 IE 41879B1
- Authority
- IE
- Ireland
- Prior art keywords
- hydroxyphenylglycine
- solution
- hydrobromide
- mixture
- aqueous
- Prior art date
Links
- 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 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 18
- 230000003287 optical effect Effects 0.000 title description 17
- 238000000746 purification Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 239000000243 solution Substances 0.000 claims abstract description 25
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 23
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims abstract description 16
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 4
- JVPZDYVRERLSBQ-UHFFFAOYSA-N Br.OC1=CC=C(C(N)C(=O)O)C=C1 Chemical compound Br.OC1=CC=C(C(N)C(=O)O)C=C1 JVPZDYVRERLSBQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 5
- 239000003513 alkali Substances 0.000 abstract description 3
- 150000001413 amino acids Chemical class 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JJVODHIRRAFJDE-UHFFFAOYSA-N 2-(hydroxyamino)-2-phenylacetic acid Chemical class ONC(C(O)=O)C1=CC=CC=C1 JJVODHIRRAFJDE-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- -1 D-p-hydroxyphenylglycine hydrobromide Chemical compound 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- KKLMJYDGZSAIQX-UHFFFAOYSA-N 2-(n-hydroxyanilino)acetic acid Chemical compound OC(=O)CN(O)C1=CC=CC=C1 KKLMJYDGZSAIQX-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 101100025412 Arabidopsis thaliana XI-A gene Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53971775A | 1975-01-09 | 1975-01-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41879L IE41879L (en) | 1976-07-09 |
| IE41879B1 true IE41879B1 (en) | 1980-04-09 |
Family
ID=24152365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2458/75A IE41879B1 (en) | 1975-01-09 | 1975-11-11 | Process for optical purification of d-p-hydroxyphenylglycine |
Country Status (13)
-
1975
- 1975-01-01 AR AR261831A patent/AR205293A1/es active
- 1975-11-11 IE IE2458/75A patent/IE41879B1/en unknown
- 1975-11-20 GB GB4787075A patent/GB1476110A/en not_active Expired
- 1975-12-23 NL NL7514992A patent/NL7514992A/xx not_active Application Discontinuation
- 1975-12-30 DK DK594175A patent/DK146801C/da not_active IP Right Cessation
- 1975-12-30 CA CA242,783A patent/CA1033760A/en not_active Expired
- 1975-12-31 FR FR7540229A patent/FR2297208A1/fr active Granted
- 1975-12-31 ES ES444002A patent/ES444002A1/es not_active Expired
- 1975-12-31 BE BE1007110A patent/BE837214A/xx not_active IP Right Cessation
-
1976
- 1976-01-02 SE SE7600016A patent/SE7600016L/xx unknown
- 1976-01-02 LU LU74131A patent/LU74131A1/xx unknown
- 1976-01-05 JP JP51000578A patent/JPS5191228A/ja active Granted
- 1976-01-06 MX MX761298U patent/MX3598E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7600016L (sv) | 1976-07-12 |
| NL7514992A (nl) | 1976-07-13 |
| AR205293A1 (es) | 1976-04-21 |
| CA1033760A (en) | 1978-06-27 |
| DE2552932B2 (de) | 1977-07-07 |
| IE41879L (en) | 1976-07-09 |
| MX3598E (es) | 1981-03-25 |
| LU74131A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-11-11 |
| DE2552932A1 (de) | 1976-07-15 |
| GB1476110A (en) | 1977-06-10 |
| AU8791775A (en) | 1977-07-07 |
| BE837214A (fr) | 1976-06-30 |
| JPS5191228A (en) | 1976-08-10 |
| ES444002A1 (es) | 1977-04-16 |
| JPS5636184B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-08-22 |
| DK146801C (da) | 1984-06-18 |
| FR2297208A1 (fr) | 1976-08-06 |
| FR2297208B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-01-27 |
| DK594175A (da) | 1976-07-10 |
| DK146801B (da) | 1984-01-09 |
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