IE32997B1 - Resolution of (cis-1,2-epoxypropyl)phosphonic acid and its optically-active forms - Google Patents
Resolution of (cis-1,2-epoxypropyl)phosphonic acid and its optically-active formsInfo
- Publication number
- IE32997B1 IE32997B1 IE1252/68A IE125268A IE32997B1 IE 32997 B1 IE32997 B1 IE 32997B1 IE 1252/68 A IE1252/68 A IE 1252/68A IE 125268 A IE125268 A IE 125268A IE 32997 B1 IE32997 B1 IE 32997B1
- Authority
- IE
- Ireland
- Prior art keywords
- salt
- optically active
- salts
- mixture
- diastereoisomeric
- Prior art date
Links
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 abstract 17
- 239000002585 base Substances 0.000 abstract 8
- 239000000203 mixture Substances 0.000 abstract 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 5
- -1 alkaline earth metal salt Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 229930013930 alkaloid Natural products 0.000 abstract 1
- 150000001361 allenes Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 150000004074 biphenyls Chemical class 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 238000004587 chromatography analysis 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
- 150000001925 cycloalkenes Chemical class 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 150000003003 phosphines Chemical class 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 abstract 1
- HISNRBVYBOVKMB-UHFFFAOYSA-N stibonium Chemical compound [SbH4+] HISNRBVYBOVKMB-UHFFFAOYSA-N 0.000 abstract 1
- 150000003585 thioureas Chemical class 0.000 abstract 1
- 150000003672 ureas Chemical class 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
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
- C07F9/1403—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-unsaturated acyclic group
-
- 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
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,239,989. Diastereoisomeric salts of antipodes of (cis - 1,2 - epoxypropyl)phosphonic acid. MERCK & CO. Inc. 24 Oct., 1968 [30 Oct., 1967; 15 May, 1968; 20 Aug., 1968], No. 50638/68. Heading C2C. A diastereoisomeric salt of an antipode of (cis - 1,2 - epoxypropyl)phosphonic acid is obtained by reacting a mixture of such antipodes or a salt thereof with an optically active salt-forming compound, and separating and recovering the said diastereoisomeric salt. The optically active salt-forming compound is preferably an optically active base and may be used in an amount sufficient to form the optically active salts of one or both ( + ) and (-) enantiomers. When the salt of one enantiomer is formed the other enantiomer can be recovered from the mixture remaining after separation of the diastereoisomeric salt and when both salts are formed, one of the salts is first separated and the other salt is then recovered. The diastereoisomeric salts formed may be converted to the free (cis - 1,2 - epoxypropyl) phosphonic acid or to a different salt thereof, e.g. to an alkali metal- or alkaline earth metal salt. The process can also be carried out by reacting a mixture of the enantiomers with a mixture of an optically active base and an optically inactive salt-forming base and separating the optically active base salt of one of the enantiomers from the resulting reaction mixture, at least one-half mole of the optically active base being preferably used per mole of the enantiomers. In this procedure the two bases may be added to a solution of a mixture of the antipodes in a solvent and the optically active salt of one of the enantiomers separated from the reaction mixture. Thus the (+) - α - phenethyl - ammonium (-)(cis - 1,2 - epoxypropyl)phosphonate crystallizes from an aqueous solution of a mixture of (+) - α - phenethylamine and triethylamine salts of the racemic phosphonic salt. The optically active bases may be for example amines, hydrazines, imines, imino-esters, hydrazides, phosphines, biphosphines, phosphonium, stibonium or sulphonium compounds, stibines, arsines, alkaloids (e.g. (-) quinine), amino steroids or amino acids and several suitable bases are specified. Optically active allenes, spiranes, biphenyls, cycloalkenes and certain substituted ethanes may also be used as saltforming compounds. The diastereoisomeric salts can be separated by fractional crystallization from suitable solvents, especially C 1 -C 5 alkanols or aqueous C 1 -C 5 alkanols, or by chromatography or by the use of ureas, thioureas, or clathrates to form inclusion products with one of the diastereoisomeric salts.
[GB1239989A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67920367A | 1967-10-30 | 1967-10-30 | |
| US72944568A | 1968-05-15 | 1968-05-15 | |
| US75385868A | 1968-08-20 | 1968-08-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE32997L IE32997L (en) | 1969-04-30 |
| IE32997B1 true IE32997B1 (en) | 1974-02-20 |
Family
ID=27418346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1252/68A IE32997B1 (en) | 1967-10-30 | 1968-10-21 | Resolution of (cis-1,2-epoxypropyl)phosphonic acid and its optically-active forms |
Country Status (17)
| Country | Link |
|---|---|
| BE (1) | BE723073A (en) |
| CH (1) | CH527224A (en) |
| DE (1) | DE1805681C3 (en) |
| DK (1) | DK139141B (en) |
| ES (1) | ES359542A1 (en) |
| FI (1) | FI51703C (en) |
| FR (1) | FR1592150A (en) |
| GB (1) | GB1239989A (en) |
| IE (1) | IE32997B1 (en) |
| IL (1) | IL30920A (en) |
| IT (1) | IT986758B (en) |
| LU (1) | LU57184A1 (en) |
| NL (1) | NL6814979A (en) |
| NO (1) | NO132992C (en) |
| OA (1) | OA03882A (en) |
| RO (1) | RO54819A (en) |
| SE (1) | SE377941B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1161974B (en) * | 1978-02-02 | 1987-03-18 | Italchemi Spa | CIS.I 2 EPOXYPROPYLPHOSPHONIC ACID DERIVATIVES THEIR PREPARATION PROCEDURE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| DE3906953A1 (en) * | 1989-03-04 | 1990-09-20 | Byk Gulden Lomberg Chem Fab | METHOD FOR PRODUCING OPTICALLY PURE OXIRANCARBONIC ACIDS |
| CN109369718A (en) * | 2018-12-07 | 2019-02-22 | 武汉工程大学 | A kind of preparation method and phosphonomycin of the right ammonium salt of left phosphorus |
-
1968
- 1968-10-18 NL NL6814979A patent/NL6814979A/xx unknown
- 1968-10-21 IL IL30920A patent/IL30920A/en unknown
- 1968-10-21 IE IE1252/68A patent/IE32997B1/en unknown
- 1968-10-22 CH CH1578668A patent/CH527224A/en not_active IP Right Cessation
- 1968-10-23 OA OA53389A patent/OA03882A/en unknown
- 1968-10-23 IT IT40661/68A patent/IT986758B/en active
- 1968-10-24 GB GB50638/68A patent/GB1239989A/en not_active Expired
- 1968-10-25 ES ES359542A patent/ES359542A1/en not_active Expired
- 1968-10-28 DE DE1805681A patent/DE1805681C3/en not_active Expired
- 1968-10-29 NO NO4277/68A patent/NO132992C/no unknown
- 1968-10-29 SE SE6814621A patent/SE377941B/xx unknown
- 1968-10-29 BE BE723073D patent/BE723073A/xx not_active IP Right Cessation
- 1968-10-29 FI FI683069A patent/FI51703C/en active
- 1968-10-29 DK DK522068AA patent/DK139141B/en not_active IP Right Cessation
- 1968-10-29 LU LU57184D patent/LU57184A1/xx unknown
- 1968-10-30 RO RO58059A patent/RO54819A/ro unknown
- 1968-10-30 FR FR1592150D patent/FR1592150A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| LU57184A1 (en) | 1969-05-16 |
| BE723073A (en) | 1969-04-29 |
| ES359542A1 (en) | 1970-10-16 |
| OA03882A (en) | 1975-08-14 |
| NO132992C (en) | 1976-02-18 |
| NL6814979A (en) | 1969-05-02 |
| GB1239989A (en) | 1971-07-21 |
| RO54819A (en) | 1973-02-17 |
| FI51703C (en) | 1977-03-10 |
| SE377941B (en) | 1975-08-04 |
| IL30920A (en) | 1973-03-30 |
| NO132992B (en) | 1975-11-10 |
| FR1592150A (en) | 1970-05-11 |
| FI51703B (en) | 1976-11-30 |
| DE1805681A1 (en) | 1969-12-11 |
| IL30920A0 (en) | 1968-12-26 |
| IE32997L (en) | 1969-04-30 |
| IT986758B (en) | 1975-01-30 |
| DK139141C (en) | 1979-05-28 |
| DE1805681C3 (en) | 1974-09-19 |
| CH527224A (en) | 1972-08-31 |
| DK139141B (en) | 1978-12-27 |
| DE1805681B2 (en) | 1974-02-14 |
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