IE32444B1 - (-) (cis-1,2-epoxypropyl)phosphonic acid derivatives - Google Patents
(-) (cis-1,2-epoxypropyl)phosphonic acid derivativesInfo
- Publication number
- IE32444B1 IE32444B1 IE1253/68A IE125368A IE32444B1 IE 32444 B1 IE32444 B1 IE 32444B1 IE 1253/68 A IE1253/68 A IE 1253/68A IE 125368 A IE125368 A IE 125368A IE 32444 B1 IE32444 B1 IE 32444B1
- Authority
- IE
- Ireland
- Prior art keywords
- salt
- epoxypropyl
- cis
- phosphonic acid
- reacting
- Prior art date
Links
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 title abstract 2
- 150000003007 phosphonic acid derivatives Chemical class 0.000 title abstract 2
- -1 methylene, ethylene, propylene Chemical group 0.000 abstract 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 150000005690 diesters Chemical class 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical class [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- 150000003573 thiols Chemical class 0.000 abstract 2
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical class C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 abstract 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- ZJEHRMYJNACSLL-UHFFFAOYSA-N 1-[butoxy(chloro)phosphoryl]oxybutane Chemical compound CCCCOP(Cl)(=O)OCCCC ZJEHRMYJNACSLL-UHFFFAOYSA-N 0.000 abstract 1
- YYTYLIVWHBVGKW-UHFFFAOYSA-N 1-[butoxy(prop-1-ynyl)phosphoryl]oxybutane Chemical compound C(CCC)OP(OCCCC)(=O)C#CC YYTYLIVWHBVGKW-UHFFFAOYSA-N 0.000 abstract 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 abstract 1
- WUEAMTVQNGYLRI-UHFFFAOYSA-N 2-dichlorophosphoryl-1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=C(P(Cl)(Cl)=O)C(C(C)C)=C1 WUEAMTVQNGYLRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 abstract 1
- XWCIXXXLOAAWPU-IHWYPQMZSA-N [(z)-prop-1-enyl]phosphonic acid Chemical compound C\C=C/P(O)(O)=O XWCIXXXLOAAWPU-IHWYPQMZSA-N 0.000 abstract 1
- DXMAARCZJITWJZ-UHFFFAOYSA-L [Mg+2].[Br-].[Br-].CC#C Chemical compound [Mg+2].[Br-].[Br-].CC#C DXMAARCZJITWJZ-UHFFFAOYSA-L 0.000 abstract 1
- 230000003213 activating effect Effects 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 150000001718 carbodiimides Chemical class 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 125000000743 hydrocarbylene group Chemical group 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 150000003009 phosphonic acids Chemical class 0.000 abstract 1
- XWCIXXXLOAAWPU-UHFFFAOYSA-N prop-1-enylphosphonic acid Chemical compound CC=CP(O)(O)=O XWCIXXXLOAAWPU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000003378 silver Chemical class 0.000 abstract 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
- C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,239,986. (-)(Bis - 1,2 - epoxypropyl)phosphonic acid derivatives. MERCK & CO. Inc. 24 Oct., 1968 [15 May, 1968; 28 Aug., 1968], No. 50631/68. Heading C2C. [Also in Division A5] The invention comprises (a) esters of (-)(cis- 1,2 - epoxypropyl)phosphonic acid of the formula wherein R is a substituted or unsubstituted hydrocarbyl or heterocyclic group, R 1 is H or an equivalent of a salt-forming cation, or a substituted or unsubstituted hydrocarbyl or heterocyclic group or R and R 1 together form a hydrocarbylene e.g. methylene, ethylene, propylene or arylene bridge, and (b) derivatives of (-) (cis - 1,2 - epoxypropyl)phosphonic acid of the formula in which Y is an -OR 2 group or a halogen atom where R 2 is C 1 -C 6 alkyl, C 1 -C 6 substituted alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, aryl, substituted aryl, aralkyl, or substituted aralkyl and Y<SP>1</SP> is a halogen atom. The hydrocarbyl or substituted hydrocarbyl radicals may be substituted or unsubstituted alkyl radicals, or alkenyl, alkynyl, cycloaliphatic, araliphatic or aromatic radicals. The esters (I) may be prepared (a) by reacting a heavy metal (preferably silver) salt of (-)(cis - 1,2 - epoxypropyl)phos. phonic acid with a halide (R Hal); (b) by reacting the free phosphonic acid with a diazoalkane or diazoaralkane, (c) by reacting (-)(cis - 1,2- epoxypropyl)phosphonic dichloride with an alcohol or phenol (ROH) conveniently in the presence of a tertiary amine, this reaction being operable to prepare mono- or di-esters by using appropriate molar proportions of the reactants, (d) by reacting a salt of the phosphonic, e.g. an alkali metal or amine salt with an alcohol or thiol in the presence of an activating agent e.g. a carbodiimide such as dicyclohexyl carbodiimide, an arylsulphonyl halide, e.g. 2,4,6- trimethylsulphonyl chloride or trichloroacetonitrile. Monoesters may also be obtained by reacting a diester with a dilute base e.g. NaOH or KOH at a pH of 8-13 to remove one ester residue. Mixed esters may be prepared (a) by reacting a (-)(cis - 1,2 - epoxypropyl)monoester phosphonohalidate with an alcohol or thiol in the presence of an acid binding agent, e.g. a tertiary amine, or (b) by converting a monoester mono-alkali metal salt to the free acid and then to the mono-silver salt by reaction with a soluble silver salt and then reacting the monosilver salt monoester with a hydrocarbyl halide the hydrocarbon residue of which is different from that of the monoester radical. Diesters may also be obtained by treatment of a 1 - chloro - 2- hydroxypropyl phosphonic acid diester with a base. The (-)(cis - 1,2 epoxypropyl)phosphonic dihalides may be obtained by reacting the free phosphonic acid with a halogenating agent, preferably a thionyl halide such as thionyl chloride. The ester and ester salt products have antibacterial properties and the diester products may be converted to monoamide derivatives of (-)(cis - 1,2 - epoxypropyl)phosphonic acid salts thereof, e.g. by hydrolysing with alkali to form a monoester which is reacted with thionyl chloride to form the monoester chloride, the latter being then reacted with an amine to form the monoester monoamide which on hydrolysis with an alkali, e.g. NaOH, forms a salt of the monoamide. The diesters may be converted to the free phosphonic acid or salts thereof by various methods e.g. as disclosed in Specification No. 1,236,955/68. Di - n - butyl cis propenylphosphonate is obtained by hydrogenation of di - n - butyl propynyl phosphonate and is converted to cispropenyl phosphonic acid by treatment with concentrated HC1 followed by the addition of water and the free acid after neutralization with NB 4 OH to pH 5À5 is epoxidized to form the ammonium salt of, ()(cis - 1,2 - epoxypropyl)- phosphonic acid which is then resolved by use of (+ )α - phenethylamine to form the (+)α- phenylethylamine salt of (-)(cis - 1,2 - epoxypropyl)phosphonic acid from which the free phosphonic acid is obtained by passing a solution of the salt over an ion exchange resin on the H<SP>+</SP> cycle. Di - n - butyl propynylphosphonate is obtained by reacting methylacetylene magnesium bromide with di - n - butyl chlorophosphonate, a detailed example being given.
[GB1239986A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72944468A | 1968-05-15 | 1968-05-15 | |
| US75580568A | 1968-08-28 | 1968-08-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE32444L IE32444L (en) | 1969-11-15 |
| IE32444B1 true IE32444B1 (en) | 1973-08-08 |
Family
ID=27111879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1253/68A IE32444B1 (en) | 1968-05-15 | 1968-10-21 | (-) (cis-1,2-epoxypropyl)phosphonic acid derivatives |
Country Status (14)
| Country | Link |
|---|---|
| AT (3) | AT299246B (en) |
| BE (1) | BE723075A (en) |
| BG (1) | BG16345A3 (en) |
| CH (1) | CH537953A (en) |
| ES (1) | ES359543A1 (en) |
| FR (1) | FR2008585B1 (en) |
| GB (1) | GB1239986A (en) |
| HU (1) | HU163312B (en) |
| IE (1) | IE32444B1 (en) |
| IL (1) | IL30921A0 (en) |
| LU (1) | LU57188A1 (en) |
| MT (1) | MTP594B (en) |
| NL (1) | NL6814984A (en) |
| ZM (1) | ZM14368A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6814984A (en) * | 1968-05-15 | 1969-11-18 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6814984A (en) * | 1968-05-15 | 1969-11-18 |
-
1968
- 1968-10-18 NL NL6814984A patent/NL6814984A/xx unknown
- 1968-10-21 IE IE1253/68A patent/IE32444B1/en unknown
- 1968-10-21 CH CH1570168A patent/CH537953A/en not_active IP Right Cessation
- 1968-10-21 IL IL30921A patent/IL30921A0/en unknown
- 1968-10-24 GB GB50631/68A patent/GB1239986A/en not_active Expired
- 1968-10-25 HU HUME999A patent/HU163312B/hu unknown
- 1968-10-25 ES ES359543A patent/ES359543A1/en not_active Expired
- 1968-10-29 LU LU57188D patent/LU57188A1/xx unknown
- 1968-10-29 BE BE723075D patent/BE723075A/xx unknown
- 1968-10-29 BG BG010911A patent/BG16345A3/en unknown
- 1968-10-30 AT AT358870A patent/AT299246B/en not_active IP Right Cessation
- 1968-10-30 AT AT358770A patent/AT299247B/en not_active IP Right Cessation
- 1968-10-30 ZM ZM143/68A patent/ZM14368A1/en unknown
- 1968-10-30 AT AT1055868A patent/AT294120B/en not_active IP Right Cessation
- 1968-12-30 MT MT594A patent/MTP594B/en unknown
-
1969
- 1969-05-14 FR FR6915696A patent/FR2008585B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BG16345A3 (en) | 1972-08-20 |
| FR2008585B1 (en) | 1973-12-21 |
| AT294120B (en) | 1971-11-10 |
| BE723075A (en) | 1969-04-29 |
| CH537953A (en) | 1973-06-15 |
| AT299247B (en) | 1972-06-12 |
| ES359543A1 (en) | 1970-08-16 |
| HU163312B (en) | 1973-07-28 |
| ZM14368A1 (en) | 1970-06-18 |
| FR2008585A1 (en) | 1970-01-23 |
| LU57188A1 (en) | 1969-05-16 |
| MTP594B (en) | 1971-04-14 |
| IE32444L (en) | 1969-11-15 |
| NL6814984A (en) | 1969-11-18 |
| GB1239986A (en) | 1971-07-21 |
| IL30921A0 (en) | 1968-12-26 |
| DE1805682A1 (en) | 1969-12-11 |
| AT299246B (en) | 1972-06-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1140980A (en) | New diphosphonic acids, derivatives thereof and detergent compositions containing them | |
| DE59906738D1 (en) | Process for the preparation of phosphinic acid esters | |
| IE40852L (en) | Fungicidal phosphonates | |
| DE50104089D1 (en) | Process for the preparation of ethane-1,2-bis (alkylphosphinic acids) | |
| US2903475A (en) | Production of esters of phosphonous and phosphinous acids | |
| DE69331314D1 (en) | Process for the preparation of N-phosphonomethyliminodiacetic acid | |
| FI894127A0 (en) | Process for Continuous Preparation of 2-Phosphonobutane-1,2,4-Tricarboxylic Acid and Its Alkali Metal Salts | |
| IE32444B1 (en) | (-) (cis-1,2-epoxypropyl)phosphonic acid derivatives | |
| GB1265167A (en) | ||
| GB1075125A (en) | Improvements relating to phosphorus-containing metal-organic compounds | |
| ATE248180T1 (en) | METHOD FOR PRODUCING PHOSPHONIC ACID ESTERS | |
| US3271481A (en) | 2, 6-disubstituted primary aryl phosphites and phosphorodihalidites and processes for the manufacture thereof | |
| ATE20668T1 (en) | PROCESS FOR THE PREPARATION OF ALKALI METAL SALTS OF 1-PHOSPHONOPROPANE-1,2,3-TRICARBONIC ACID. | |
| EP0061106A3 (en) | Process for preparing oligophosphonic acids or oligophosphinic acids, their salts and/or esters, as well as phosphonic and phosphinic acid derivatives | |
| GB1274350A (en) | 2-chloroethane-(thiono)-phosphonic acid derivatives, process for their preparation, and their use for the regulation of plant growth | |
| GB934090A (en) | Chloromethylphosphinic acid, salts thereof, and method of preparation | |
| ATE3404T1 (en) | PROCESS FOR THE PREPARATION OF 1,1-DIHALOGENALKENES. | |
| GB1398844A (en) | Manufacture of 1-hydroxyethane 1,1-diphosphonic acid | |
| GB702750A (en) | Synthesis of pantothenic acid-4 phosphate | |
| DE2846835A1 (en) | METHOD FOR PRODUCING CARBOXYLALKANE-AMINOALKANE DIPHOSPHONIC ACIDS AND AMINOARYLALKANE DIPHOSPHONIC ACIDS | |
| ES367106A1 (en) | Preparation of (cis-1,2-epoxypropyl)phosphonic acid and its salts and esters | |
| US3007952A (en) | Organo-phosphorus compounds and preparation | |
| KR910018392A (en) | Process for preparing phosphono organo carboxylic acid | |
| GB1512185A (en) | Process for conditioning fibres and heat-resistant fibre-conditioning agents therefor | |
| GB1212931A (en) | Phosphorus compounds containing phosphorus to carbon linkages |