GB1236957A - Preparation of (cis-1,2-epoxypropyl)phosphonic acid and derivatives - Google Patents
Preparation of (cis-1,2-epoxypropyl)phosphonic acid and derivativesInfo
- Publication number
- GB1236957A GB1236957A GB23974/69A GB2397469A GB1236957A GB 1236957 A GB1236957 A GB 1236957A GB 23974/69 A GB23974/69 A GB 23974/69A GB 2397469 A GB2397469 A GB 2397469A GB 1236957 A GB1236957 A GB 1236957A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cis
- epoxypropyl
- acid
- phosphonic acid
- salts
- 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
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title 1
- -1 1,2 - epoxypropyl Chemical group 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 abstract 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 abstract 1
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 abstract 1
- ZRWLFJLOPUKBNC-UHFFFAOYSA-N 3-hydroxy-2-methylprop-2-enenitrile Chemical compound OC=C(C)C#N ZRWLFJLOPUKBNC-UHFFFAOYSA-N 0.000 abstract 1
- VGKZBAMIYUHSMU-UHFFFAOYSA-N 4-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(NC(=O)N(CCCl)N=O)CC1 VGKZBAMIYUHSMU-UHFFFAOYSA-N 0.000 abstract 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract 1
- 235000001258 Cinchona calisaya Nutrition 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 238000005377 adsorption chromatography Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 229940012017 ethylenediamine Drugs 0.000 abstract 1
- 238000004817 gas chromatography Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- 229960000948 quinine Drugs 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- UCVPBPFMIUPTQM-UHFFFAOYSA-N tris(4-nitrophenyl) phosphite Chemical compound C1=CC([N+](=O)[O-])=CC=C1OP(OC=1C=CC(=CC=1)[N+]([O-])=O)OC1=CC=C([N+]([O-])=O)C=C1 UCVPBPFMIUPTQM-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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,236,957. Preparing ( )(cis 1,2 - epoxypropyl) - phosphonic acid and derivatives thereof. MERCK & CO. Inc. 12 May, 1969 [15 May, 1968], No. 23974/69. Heading C2C. A ( )(cis 1,2 - epoxypropyl) - phosphonic acid diester is obtained by reacting 2-cyano-1 hydroxy-propene with a phosphite triester having the formula P(OR) 3 wherein R is a C 1 -C 5 alkyl, C 2 -C 5 alkenyl, mononuclear aralkyl, e.g. benzyl, or nitro-substituted mononuclear aryl, e.g. 4-nitro phenyl or 2,4-dinitrophenyl. The isomeric mixture of the ester derivatives of ( )(cis 1,2-epoxypropyl)-phosphonic acid obtained as product may be separated by gas- or adsorption chromatography to yield the ester derivatives of the ( ) cis and trans isomers and the esters of the ( ) cis acid can be converted to ( )(cis 1,2-epoxypropyl)- phosphonic acid, e.g. by U.V. irradiation, acid hydrolysis under buffered conditions, enzymolysis, or catalytic hydrogenation using Raney nickel and salts of the acid may be obtained by treating the acid with a suitable base or amine. Specified salts are the Na, Ca and Mg salts and the salts derived from diethylamine, benzylamine, ethylene - diamine, α- phenethylamine and quinine. The main reaction may be carried out in a solvent and is suitably effected at from 15 to 120 C. The products have antibacterial properties. Tri - (4 - nitrophenyl) - phosphite is obtained by adding PCl 3 to a solution of 4-nitrophenol and N,N-dimethylaniline in ether at 10 C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72941268A | 1968-05-15 | 1968-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1236957A true GB1236957A (en) | 1971-06-23 |
Family
ID=24930913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23974/69A Expired GB1236957A (en) | 1968-05-15 | 1969-05-12 | Preparation of (cis-1,2-epoxypropyl)phosphonic acid and derivatives |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE733044A (en) |
| CH (1) | CH518984A (en) |
| DE (1) | DE1924260A1 (en) |
| ES (1) | ES367103A1 (en) |
| GB (1) | GB1236957A (en) |
| IL (1) | IL32130A0 (en) |
| NL (1) | NL6905052A (en) |
| SE (1) | SE362434B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2179944A (en) * | 1985-09-03 | 1987-03-18 | Espan Penicilin & Antibioticos | Mixtures of mono- and disodium salts of fosfomycin |
| WO2010037639A1 (en) * | 2008-10-02 | 2010-04-08 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e. V. | 1,2-epoxypropylphosphonic acid and derivatives thereof for flame-retardant plastics |
-
1969
- 1969-04-01 SE SE04614/69A patent/SE362434B/xx unknown
- 1969-04-01 NL NL6905052A patent/NL6905052A/xx unknown
- 1969-05-01 IL IL32130A patent/IL32130A0/en unknown
- 1969-05-12 ES ES367103A patent/ES367103A1/en not_active Expired
- 1969-05-12 DE DE19691924260 patent/DE1924260A1/en active Pending
- 1969-05-12 GB GB23974/69A patent/GB1236957A/en not_active Expired
- 1969-05-14 CH CH742569A patent/CH518984A/en not_active IP Right Cessation
- 1969-05-14 BE BE733044D patent/BE733044A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2179944A (en) * | 1985-09-03 | 1987-03-18 | Espan Penicilin & Antibioticos | Mixtures of mono- and disodium salts of fosfomycin |
| WO2010037639A1 (en) * | 2008-10-02 | 2010-04-08 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e. V. | 1,2-epoxypropylphosphonic acid and derivatives thereof for flame-retardant plastics |
Also Published As
| Publication number | Publication date |
|---|---|
| ES367103A1 (en) | 1971-06-16 |
| CH518984A (en) | 1972-02-15 |
| DE1924260A1 (en) | 1970-01-22 |
| SE362434B (en) | 1973-12-10 |
| NL6905052A (en) | 1969-11-18 |
| BE733044A (en) | 1969-11-14 |
| IL32130A0 (en) | 1969-07-30 |
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