PL410604A1 - Diastereoselective method for producing alpha-aminophosphonic acids - Google Patents
Diastereoselective method for producing alpha-aminophosphonic acidsInfo
- Publication number
- PL410604A1 PL410604A1 PL410604A PL41060414A PL410604A1 PL 410604 A1 PL410604 A1 PL 410604A1 PL 410604 A PL410604 A PL 410604A PL 41060414 A PL41060414 A PL 41060414A PL 410604 A1 PL410604 A1 PL 410604A1
- Authority
- PL
- Poland
- Prior art keywords
- alpha
- configuration
- aminophosphonic acids
- solvent
- general formula
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 150000001721 carbon Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- -1 C1-C6 perhaloalkyl Chemical group 0.000 abstract 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 abstract 1
- 239000012038 nucleophile Substances 0.000 abstract 1
- 239000012044 organic layer Substances 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
Abstract
Przedmiotem wynalazku jest wysoce diastereoselektywny sposób wytwarzania kwasów alfa-aminofosfonowych o konfiguracji R na atomie węgla alfa i wzorze ogólnym 1, w którym R1 stanowi grupą C1-C12 alkilową, C6-C14 arylową, która korzystnie podstawiona jest co najmniej jedną grupą C1-C6 alkilową, C1-C6 perhalogenoalkilową, C1-C6 alkoksylową lub atomem fluorowca. Sposób polega na tym, że w pierwszym etapie chiralny nukleofil fosforowy będący fosforową pochodną TADDOL-u poddaje się reakcji z odpowiednią tert-butylosulfoniminą o konfiguracji S na atomie siarki oraz bezwodnym K2CO3 w stosunku molowym 1:1:1 w CH2Cl2 w temperaturze pokojowej przez 12 godzin. Następnie odparowuje się rozpuszczalnik, wydzielając w wyniku chromatografii kolumnowej główny diastereoizomer alfa-aminofosfonianu, w którym R1 ma podane wyżej znaczenie, który w drugim etapie rozpuszcza się w toluenie, dodaje się 4M wodnego kwasu solnego, w stosunku 1 do 10 i ogrzewa się w temperaturze 80°C, przez 4 h. Odrzuca się warstwę organiczną, a z warstwy wodnej przez odparowanie rozpuszczalnika i zadanie pozostałości alkoholem etylowym wydziela się odpowiednie kwasy alfa-aminofosfonowe o konfiguracji R na atomie węgla alfa i wzorze ogólnym 1 w postaci krystalicznej.The subject of the invention is a highly diastereoselective process for the production of alpha-aminophosphonic acids with the R configuration on the alpha carbon atom and general formula 1, wherein R1 is a C1-C12 alkyl group, C6-C14 aryl group which is preferably substituted by at least one C1-C6 alkyl group , C1-C6 perhaloalkyl, C1-C6 alkoxy or halogen. The method consists in the fact that in the first stage a chiral phosphorus nucleophile being a phosphorus derivative of TADDOL is reacted with the appropriate tert-butylsulfonimine with the S configuration on the sulfur atom and anhydrous K2CO3 in a molar ratio of 1: 1: 1 in CH2Cl2 at room temperature for 12 hours. The solvent is then evaporated, separating by column chromatography the main alpha-aminophosphonate diastereomer, in which R1 is as defined above, which in the second stage dissolves in toluene, 4M aqueous hydrochloric acid is added in a ratio of 1 to 10 and heated at a temperature of 80 ° C, for 4 h. The organic layer is discarded, and the aqueous layer by evaporation of the solvent and treatment of the residue with ethyl alcohol separates the corresponding alpha-aminophosphonic acids with the R configuration on the alpha carbon atom and general formula 1 in crystalline form.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL410604A PL231856B1 (en) | 2014-12-22 | 2014-12-22 | Diastereoselective method for producing alpha-aminophosphonic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL410604A PL231856B1 (en) | 2014-12-22 | 2014-12-22 | Diastereoselective method for producing alpha-aminophosphonic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL410604A1 true PL410604A1 (en) | 2015-10-26 |
| PL231856B1 PL231856B1 (en) | 2019-04-30 |
Family
ID=54330484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL410604A PL231856B1 (en) | 2014-12-22 | 2014-12-22 | Diastereoselective method for producing alpha-aminophosphonic acids |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL231856B1 (en) |
-
2014
- 2014-12-22 PL PL410604A patent/PL231856B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL231856B1 (en) | 2019-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EA202090917A1 (en) | OBTAINING PSILOCYBIN, DIFFERENT POLYMORPHOUS FORMS, INTERMEDIATE COMPOUNDS, COMPOSITIONS AND THEIR APPLICATION | |
| CY1123658T1 (en) | METHOD FOR MAKING QUINOLONE COMPOUNDS | |
| JO3783B1 (en) | High purity quinoline derivative and method for its production | |
| RU2017102355A (en) | METHOD FOR PRODUCING A CONDENSED HETEROCYCLIC COMPOUND | |
| PE20180233A1 (en) | NEW BICYCLE COMPOUNDS AS DUAL ATX / AC INHIBITORS | |
| ES2721662T3 (en) | Process for the preparation of travoprost | |
| EA201992421A1 (en) | METHOD OF OBTAINING OZANIMODA | |
| EA201891437A1 (en) | METHOD FOR SEPARATION OF PIPERAZINE DERIVATIVE ENANTIOMERS | |
| PE20181039A1 (en) | METHOD FOR PREPARING SUBSTITUTE 3- (2-ANILINO-1-CYCLOHEXIL-1H-BENZYMIDAZOLE-5-IL) ACID DERIVATIVES | |
| AR117002A2 (en) | PROCESS FOR THE PREPARATION OF KINASE C-FMS INHIBITORS | |
| CY1117087T1 (en) | PROCEDURE FOR STANDARD PREPARATION (5-FLUOR-2-Methyl-3-quinolin-2-ylmethyl-indol-1-yl) - ACIC ACID | |
| EA201391721A1 (en) | METHOD OF OBTAINING POLYMORPHIC FORM I ETHORIKOXIB | |
| BR112015023343A2 (en) | method of preparing sovaprevir, method of preparing a compound of formula (c), method of preparing compound f-2, compound, process, method of preparing a pure amorphous form of sovaprevir, and crystalline form of sovaprevir | |
| PL410604A1 (en) | Diastereoselective method for producing alpha-aminophosphonic acids | |
| RU2011143166A (en) | NEW CRYSTAL FORMS OF ADEFOVIR DIPIVOXIL AND METHODS OF ITS PRODUCTION | |
| PL410605A1 (en) | Diastereoselective method for producing alpha-aminophosphonic acids | |
| TW201613856A (en) | Method for producing harmful-organism control agent, and intermediate thereof | |
| CA2928305C (en) | A crystalline anhydrous form of cabazitaxel, process for the preparation and pharmaceutical compositions thereof | |
| PL403137A1 (en) | Method for for producing an optically active alpha-aminomethyl phosphonic acids | |
| RU2014111398A (en) | SUBSTITUTED DIPEPTIDES WITH NEUROPSYCHOTROPIC ACTIVITY | |
| MX2019009311A (en) | Substituted benzyl-4-aminopicolinic esters and pyrimidino-4-carboxylic esters, methods for the production thereof, and use thereof as herbicides and plant growth regulators. | |
| AR086926A1 (en) | IMIDAZOL DERIVATIVES PRODUCTION METHOD | |
| PL403136A1 (en) | Method for for producing optically active alpha-hydroxymethyl phosphonic acids | |
| PL404606A1 (en) | Method for the preparation of 1,3,5-triarylbenzene and truxene derivatives | |
| PL446966A1 (en) | Asymmetric method for producing chiral 1-hydroxyphosphonates |