CA1109079A - Process for the preparation of dl-phenyl-glycine amide - Google Patents
Process for the preparation of dl-phenyl-glycine amideInfo
- Publication number
- CA1109079A CA1109079A CA316,693A CA316693A CA1109079A CA 1109079 A CA1109079 A CA 1109079A CA 316693 A CA316693 A CA 316693A CA 1109079 A CA1109079 A CA 1109079A
- Authority
- CA
- Canada
- Prior art keywords
- phenylglycine
- ester
- acid
- amide
- reaction mixture
- 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 abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 title description 6
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 18
- KIYRSYYOVDHSPG-UHFFFAOYSA-N 2-amino-2-phenylacetamide Chemical compound NC(=O)C(N)C1=CC=CC=C1 KIYRSYYOVDHSPG-UHFFFAOYSA-N 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000006340 racemization Effects 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 239000001117 sulphuric acid Substances 0.000 claims description 7
- 235000011149 sulphuric acid Nutrition 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 150000001413 amino acids Chemical class 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- -1 oleum Chemical compound 0.000 description 7
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- KIYRSYYOVDHSPG-SSDOTTSWSA-N (2r)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-SSDOTTSWSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7713189 | 1977-11-30 | ||
| NLAANVRAGE7713189,A NL188037C (nl) | 1977-11-30 | 1977-11-30 | Werkwijze voor de bereiding van dl-fenylglycine-amide via racemisatie. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1109079A true CA1109079A (en) | 1981-09-15 |
Family
ID=19829648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA316,693A Expired CA1109079A (en) | 1977-11-30 | 1978-11-22 | Process for the preparation of dl-phenyl-glycine amide |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0002297B1 (en]) |
| JP (1) | JPS5484545A (en]) |
| CA (1) | CA1109079A (en]) |
| DE (1) | DE2860487D1 (en]) |
| DK (1) | DK144677C (en]) |
| ES (1) | ES475527A1 (en]) |
| IT (1) | IT1106062B (en]) |
| MX (1) | MX5530E (en]) |
| NL (1) | NL188037C (en]) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8501093A (nl) * | 1985-04-12 | 1986-11-03 | Stamicarbon | Werkwijze voor het racemiseren van een optisch aktief n- benzylideenaminozuuramide. |
| USD685269S1 (en) | 2012-04-04 | 2013-07-02 | Colgate-Palmolive Company | Container |
| USD688951S1 (en) | 2012-04-04 | 2013-09-03 | Colgate-Palmolive Company | Container |
| USD685270S1 (en) | 2012-04-04 | 2013-07-02 | Colgate-Palmolive Company | Container |
| USD685271S1 (en) | 2012-04-04 | 2013-07-02 | Colgate-Palmolive Company | Container |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4867246A (en]) * | 1971-12-20 | 1973-09-13 | ||
| US3832388A (en) * | 1972-09-07 | 1974-08-27 | R Lorenz | Resolution of 2-(p-hydroxy)phenylglycine |
| US3933902A (en) * | 1973-04-17 | 1976-01-20 | Asahi Kasei Kogyo Kabushiki Kaisha | Method for the optical resolution of DL-αphenylglycine |
| NL7514300A (nl) * | 1975-12-09 | 1977-06-13 | Stamicarbon | Werkwijze voor de bereiding van optisch actief fenylglycineamide. |
-
1977
- 1977-11-30 NL NLAANVRAGE7713189,A patent/NL188037C/xx not_active IP Right Cessation
-
1978
- 1978-11-22 CA CA316,693A patent/CA1109079A/en not_active Expired
- 1978-11-24 DK DK525078A patent/DK144677C/da active
- 1978-11-25 DE DE7878200316T patent/DE2860487D1/de not_active Expired
- 1978-11-25 EP EP78200316A patent/EP0002297B1/en not_active Expired
- 1978-11-28 JP JP14707378A patent/JPS5484545A/ja active Granted
- 1978-11-28 MX MX787561U patent/MX5530E/es unknown
- 1978-11-29 ES ES475527A patent/ES475527A1/es not_active Expired
- 1978-11-29 IT IT52123/78A patent/IT1106062B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5484545A (en) | 1979-07-05 |
| NL188037C (nl) | 1992-03-16 |
| IT1106062B (it) | 1985-11-11 |
| JPS6323187B2 (en]) | 1988-05-16 |
| NL7713189A (nl) | 1979-06-01 |
| ES475527A1 (es) | 1979-04-01 |
| DE2860487D1 (en) | 1981-03-26 |
| EP0002297A2 (en) | 1979-06-13 |
| DK144677B (da) | 1982-05-10 |
| DK525078A (da) | 1979-05-31 |
| NL188037B (nl) | 1991-10-16 |
| EP0002297A3 (en) | 1979-06-27 |
| EP0002297B1 (en) | 1981-02-11 |
| MX5530E (es) | 1983-09-23 |
| DK144677C (da) | 1982-11-29 |
| IT7852123A0 (it) | 1978-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |