SU213863A1 - METHOD FOR PREPARING N-ALKYL ETHERS OF METHIONIN THYOPHOSPHORIC ACID - Google Patents
METHOD FOR PREPARING N-ALKYL ETHERS OF METHIONIN THYOPHOSPHORIC ACIDInfo
- Publication number
- SU213863A1 SU213863A1 SU1123840A SU1123840A SU213863A1 SU 213863 A1 SU213863 A1 SU 213863A1 SU 1123840 A SU1123840 A SU 1123840A SU 1123840 A SU1123840 A SU 1123840A SU 213863 A1 SU213863 A1 SU 213863A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- thyophosphoric
- methionin
- preparing
- alkyl ethers
- Prior art date
Links
- FFEARJCKVFRZRR-UHFFFAOYSA-N DL-methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- HPFKOFNYNQMWEF-UHFFFAOYSA-L chloro-dioxido-sulfanylidene-$l^{5}-phosphane Chemical class [O-]P([O-])(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-L 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- -1 alkyl chlorothiophosphates amides Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- ARJXIGOIOGJAKR-LURJTMIESA-N ethyl (2S)-2-amino-4-methylsulfanylbutanoate Chemical compound CCOC(=O)[C@@H](N)CCSC ARJXIGOIOGJAKR-LURJTMIESA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 150000002741 methionine derivatives Chemical class 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к способу получени новых фосфорорганических соединений общей формулыThis invention relates to a process for the preparation of novel organophosphorus compounds of the general formula
ROv /ROv /
Р-NHCHCOOR, R/IP-NHCHCOOR, R / I
R где R и R - низшие алкилы;R where R and R are lower alkyls;
R - алкоксил или алкиламин; R - (СН,)25СНз.R is alkoxy or alkylamine; R - (CH,) 25 SNC.
Соединени получают взаимодействием диалкилхлортиофосфатов или амидов алкилхлортиофосфатов с эфирами метионина в присутствии акцептора хлористого водорода. Реакцию провод т в среде органического растворител - хлороформе, бензоле, четыреххлористом углероде или этилацетате.The compounds are prepared by reacting dialkyl chlorothiophosphates or alkyl chlorothiophosphates amides with methionine esters in the presence of a hydrogen chloride acceptor. The reaction is carried out in the medium of an organic solvent — chloroform, benzene, carbon tetrachloride or ethyl acetate.
Пример. Получение N-э т и л о в о г о эфира метиопина 0,0-д иалкилтиофосфорной кислоты.Example. Preparation of N-th and l o v o g o methiopine ester of 0.0-d alkyl alkyl thiophosphoric acid.
// (С2Н50)2 Р-NH-CH-СООС,Н.,// (С2Н50) 2 Р-NH-CH-СООС, Н.,
20°С постепенно прибавл ют 0,1 моль этилового эфира метионина и 0,15 люль триэтиломина . Температура при этом поднимаетс до 45°С. Затем реакцию выдерживают при комнатной температуре в течение 18 час. Смесь промывают водой, сушат над сульфатом магни , отфильтровывают и отгон ют растворитель , а остаток фракционируют в вакууме.20 ° C gradually add 0.1 mol of methionine ethyl ester and 0.15% triethylamine. The temperature then rises to 45 ° C. Then the reaction is maintained at room temperature for 18 hours. The mixture is washed with water, dried over magnesium sulfate, filtered and the solvent is distilled off, and the residue is fractionated in vacuo.
Выделенный продукт имеет следующие константы: т. кип. 132-136°С (0,15 мм рт. ст.);The selected product has the following constants: T. Kip. 132-136 ° C (0.15 mm Hg. Art.);
По 1,4960; df 1,1403. Выход 43,5%.1.4960 each; df 1.1403. Yield 43.5%.
Аналогично получают продукты конденсации этилового эфира метионина с О,О-диалкилхлортиофосфатами и амидами 0-алкилхлортиофосфатов . Константы, выход и анализ их приведены в таблице.Similarly, the condensation products of methionine ethyl ester with O, O-dialkyl chlorothiophosphates and amides of 0-alkyl chlorothiophosphates are obtained. Constants, output and analysis of them are given in the table.
Предмет изобретени Subject invention
Способ получени Ы-алкиловых эфиров метионина тиофосфорной кислоты общей формулыThe method of obtaining N-alkyl esters of methionine thiophosphoric acid of the general formula
RO. //RO. //
Р-NHCHCOOR R/IP-NHCHCOOR R / I
RR
отличающийс тем, что диалкилхлортиофосфаты или амиды алкилхлортиофосфатов подвергают взаимодействию с эфирами метионина в присутствии акцептора хлористого водорода.characterized in that the dialkyl chlorothiophosphates or alkyl chlorothiophosphates amides are reacted with methionine esters in the presence of a hydrogen chloride acceptor.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU213863A1 true SU213863A1 (en) |
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