PL403137A1 - Method for for producing an optically active alpha-aminomethyl phosphonic acids - Google Patents
Method for for producing an optically active alpha-aminomethyl phosphonic acidsInfo
- Publication number
- PL403137A1 PL403137A1 PL403137A PL40313713A PL403137A1 PL 403137 A1 PL403137 A1 PL 403137A1 PL 403137 A PL403137 A PL 403137A PL 40313713 A PL40313713 A PL 40313713A PL 403137 A1 PL403137 A1 PL 403137A1
- Authority
- PL
- Poland
- Prior art keywords
- optically active
- stage
- formula
- alkyl group
- ratio
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- -1 C1-C6 perhaloalkyl Chemical group 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 239000010410 layer Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000012044 organic layer Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
Abstract
Przedmiotem wynalazku jest sposób wytwarzania optycznie czynnych kwasów ?-aminometylofosfonowych o wzorze 1, który polega na tym, ze w pierwszym etapie optycznie czysty lub w postaci mieszaniny racemicznej ?-hydroksymetylofosfonian o wzorze 2, w którym R1 oznacza grupe C1-C12 alkilowa, C3-C12 cykloalkilowa, C5-C14 arylowa która korzystnie podstawiona jest co najmniej jedna grupa C1-C6 alkilowa, C1-C6 perhalogenoalkilowa, C1-C6 alkoksylowa lub atomem fluorowca poddaje sie reakcji z trifenylofosfina i estrem izopropylowym kwasu azodikarboksylowego, uzytych w stosunku od 2,43 do 2,5 w obecnosci nadmiaru 1 molowego roztworu azotowodoru w benzenie. W drugim etapie otrzymane azydki poddaje sie reakcji z trifenylofosfina uzyta w stosunku 1 do 0,7 odparowuje sie rozpuszczalnik i otrzymuje sie surowe optycznie czyste ?-aminometylofosfoniany w postaci czystego diastereoizomery o wzorze 3, w którym R1 oznacza grupe C1 -C12 alkilowa, C3-C12 cykloalkilowa, C5-C14 arylowa, która korzystnie podstawiona jest najmniej jedna grupa C1-C6 alkilowa, C1-C6 perhalogenoalkilowa, C1-C6 alkoksylowa lub atomem fluorowca, które w trzecim etapie rozpuszcza sie w toluenie, dodaje sie 1M kwasu solnego, w stosunku od 1 do 10 i ogrzewa sie mieszanine reakcyjna w temperaturze 100°C, korzystnie przez 3 h. Nastepnie odrzuca sie warstwe organiczna, a z warstwy wodnej przez odparowanie rozpuszczalnika i zadanie pozostalosci alkoholem etylowym i tlenkiem propylenu wydziela sie odpowiednie optycznie czynne kwasy ?-aminometylofosfonowe jako jeden enancjomer w postaci krystalicznej.The subject of the invention is a process for the preparation of optically active α-aminomethylphosphonic acids of formula 1, which consists in optically pure or in the form of a racemic mixture of the α-hydroxymethylphosphonate of formula 2 in the first stage, wherein R1 is a C1-C12 alkyl group, C3- C12 cycloalkyl, C5-C14 aryl which is preferably substituted with at least one C1-C6 alkyl, C1-C6 perhaloalkyl, C1-C6 alkoxy or halogen is reacted with triphenylphosphine and isodyl carboxylic acid ester in a ratio of from 2.43 up to 2.5 in the presence of an excess of 1 molar hydrogen chloride in benzene. In the second stage, the azides obtained are reacted with triphenylphosphine used in a ratio of 1 to 0.7, the solvent is evaporated and crude optically pure α-aminomethylphosphonates are obtained in the form of pure diastereomers of formula 3 in which R1 is a C1-C12 alkyl group, C3- C12 cycloalkyl, C5-C14 aryl which is preferably substituted with at least one C1-C6 alkyl group, C1-C6 perhaloalkyl, C1-C6 alkoxy or halogen atom which are dissolved in toluene in the third stage, 1M hydrochloric acid is added in a ratio from 1 to 10 and the reaction mixture is heated at 100 ° C, preferably for 3 h. The organic layer is then discarded, and the aqueous layer by evaporation of the solvent and residue residue with ethyl alcohol and propylene oxide separates the corresponding optically active α-aminomethylphosphonic acids as one enantiomer in crystalline form.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL403137A PL221457B1 (en) | 2013-03-13 | 2013-03-13 | Method for for producing an optically active α-aminomethyl phosphonic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL403137A PL221457B1 (en) | 2013-03-13 | 2013-03-13 | Method for for producing an optically active α-aminomethyl phosphonic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL403137A1 true PL403137A1 (en) | 2013-09-30 |
| PL221457B1 PL221457B1 (en) | 2016-04-29 |
Family
ID=49231116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL403137A PL221457B1 (en) | 2013-03-13 | 2013-03-13 | Method for for producing an optically active α-aminomethyl phosphonic acids |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL221457B1 (en) |
-
2013
- 2013-03-13 PL PL403137A patent/PL221457B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL221457B1 (en) | 2016-04-29 |
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