IL50311A - Dimethyl alkoxy-2-oxoalkyl phosphonates and their preparattion - Google Patents
Dimethyl alkoxy-2-oxoalkyl phosphonates and their preparattionInfo
- Publication number
- IL50311A IL50311A IL7350311A IL5031173A IL50311A IL 50311 A IL50311 A IL 50311A IL 7350311 A IL7350311 A IL 7350311A IL 5031173 A IL5031173 A IL 5031173A IL 50311 A IL50311 A IL 50311A
- Authority
- IL
- Israel
- Prior art keywords
- mmole
- minutes
- dimethyl
- acetic acid
- oxo
- Prior art date
Links
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 50
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
- 229960000583 acetic acid Drugs 0.000 description 18
- 238000001228 spectrum Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 125000000457 gamma-lactone group Chemical group 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- ATYJLCKMZHNOTP-UHFFFAOYSA-N 1-dimethoxyphosphoryl-5-ethoxypentan-2-one Chemical compound CCOCCCC(=O)CP(=O)(OC)OC ATYJLCKMZHNOTP-UHFFFAOYSA-N 0.000 description 3
- QNKDUODKHMGQFR-UHFFFAOYSA-N 1-dimethoxyphosphoryl-6-methoxyhexan-2-one Chemical compound O=C(CP(OC)(OC)=O)CCCCOC QNKDUODKHMGQFR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- KXJQONGIRYVMNN-UHFFFAOYSA-N methyl 5-methoxypentanoate Chemical compound COCCCCC(=O)OC KXJQONGIRYVMNN-UHFFFAOYSA-N 0.000 description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- XBIAKGOSPOTENR-UHFFFAOYSA-N 1-dimethoxyphosphoryl-4-ethoxybutan-2-one Chemical compound CCOCCC(=O)CP(=O)(OC)OC XBIAKGOSPOTENR-UHFFFAOYSA-N 0.000 description 1
- MZMOPYFNDDILMI-UHFFFAOYSA-N 1-dimethoxyphosphoryl-5-methoxypentan-2-one Chemical compound COCCCC(=O)CP(=O)(OC)OC MZMOPYFNDDILMI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- NQYKGEPHDRUFJL-UHFFFAOYSA-N ethyl 4-ethoxybutanoate Chemical compound CCOCCCC(=O)OCC NQYKGEPHDRUFJL-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VHDGWXQBVWAMJA-UHFFFAOYSA-N methyl 4-methoxybutanoate Chemical compound COCCCC(=O)OC VHDGWXQBVWAMJA-UHFFFAOYSA-N 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25921572A | 1972-06-02 | 1972-06-02 | |
| US05/355,644 US4094899A (en) | 1972-06-02 | 1973-04-30 | Oxaprostaglandins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL50311A true IL50311A (en) | 1977-08-31 |
Family
ID=26947161
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL7350311A IL50311A (en) | 1972-06-02 | 1973-05-28 | Dimethyl alkoxy-2-oxoalkyl phosphonates and their preparattion |
| IL42373A IL42373A (en) | 1972-06-02 | 1973-05-28 | Oxaprostagliandins and their preparation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42373A IL42373A (en) | 1972-06-02 | 1973-05-28 | Oxaprostagliandins and their preparation |
Country Status (19)
| Country | Link |
|---|---|
| JP (3) | JPS5314062B2 (ja) |
| AR (2) | AR199300A1 (ja) |
| CA (1) | CA1095034A (ja) |
| CH (3) | CH590224A5 (ja) |
| DD (2) | DD124594A5 (ja) |
| DE (2) | DE2327813A1 (ja) |
| DK (1) | DK143498C (ja) |
| ES (2) | ES441003A1 (ja) |
| FI (1) | FI55995C (ja) |
| GB (3) | GB1440603A (ja) |
| IE (1) | IE38568B1 (ja) |
| IL (2) | IL50311A (ja) |
| IN (1) | IN138739B (ja) |
| LU (1) | LU67738A1 (ja) |
| NL (1) | NL162902C (ja) |
| NO (1) | NO145438C (ja) |
| PH (3) | PH11300A (ja) |
| SE (4) | SE415756B (ja) |
| YU (1) | YU36497B (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES416865A1 (es) * | 1972-07-13 | 1976-03-01 | Pfizer | Procedimiento para preparar w-pentanorprostaglandinas sus- tituidas en la posicion 15. |
| WO2021040628A1 (en) | 2019-08-28 | 2021-03-04 | Igloocompany Pte. Ltd. | System and method for controlling multiple locks |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538120A (en) * | 1967-05-22 | 1970-11-03 | Ciba Geigy Corp | Cyclopentyl-alkanoic acids |
| ZA721159B (en) * | 1971-03-22 | 1972-12-27 | Ici Ltd | Process for the separation of the c-15 epimers of 20-ethyl-9a,11alpha,15-trihydroxy-5-cis-13-trans-prostadienoic acid |
-
1973
- 1973-05-28 IL IL7350311A patent/IL50311A/en unknown
- 1973-05-28 SE SE7307521A patent/SE415756B/xx unknown
- 1973-05-28 IL IL42373A patent/IL42373A/en unknown
- 1973-05-29 FI FI1735/73A patent/FI55995C/fi active
- 1973-05-30 GB GB2306775A patent/GB1440603A/en not_active Expired
- 1973-05-30 GB GB2584673A patent/GB1440601A/en not_active Expired
- 1973-05-30 IN IN1265/CAL/73A patent/IN138739B/en unknown
- 1973-05-30 GB GB2306575A patent/GB1440602A/en not_active Expired
- 1973-06-01 DK DK303973A patent/DK143498C/da not_active IP Right Cessation
- 1973-06-01 CH CH797573A patent/CH590224A5/xx not_active IP Right Cessation
- 1973-06-01 DE DE2327813A patent/DE2327813A1/de not_active Withdrawn
- 1973-06-01 DE DE2344838A patent/DE2344838C3/de not_active Expired
- 1973-06-01 CA CA173,035A patent/CA1095034A/en not_active Expired
- 1973-06-01 CH CH415476A patent/CH589074A5/xx not_active IP Right Cessation
- 1973-06-01 CH CH415576A patent/CH586716A5/xx not_active IP Right Cessation
- 1973-06-01 IE IE881/73A patent/IE38568B1/xx unknown
- 1973-06-02 JP JP6244973A patent/JPS5314062B2/ja not_active Expired
- 1973-06-04 YU YU01469/73A patent/YU36497B/xx unknown
- 1973-06-04 PH PH14690A patent/PH11300A/en unknown
- 1973-06-04 NL NL7307740.A patent/NL162902C/xx not_active IP Right Cessation
- 1973-06-04 DD DD182818A patent/DD124594A5/xx unknown
- 1973-06-04 LU LU67738A patent/LU67738A1/xx unknown
- 1973-06-04 AR AR248400A patent/AR199300A1/es active
- 1973-06-04 DD DD171300A patent/DD109859A5/xx unknown
-
1974
- 1974-01-29 AR AR252103A patent/AR203386A1/es active
- 1974-03-11 NO NO740849A patent/NO145438C/no unknown
-
1975
- 1975-04-07 PH PH17029A patent/PH11931A/en unknown
- 1975-04-07 PH PH17030A patent/PH12035A/en unknown
- 1975-09-16 ES ES441003A patent/ES441003A1/es not_active Expired
- 1975-09-16 ES ES441002A patent/ES441002A1/es not_active Expired
-
1976
- 1976-07-19 SE SE7608221A patent/SE418857B/xx unknown
- 1976-07-19 SE SE7608222A patent/SE7608222L/xx unknown
- 1976-07-19 SE SE7608223A patent/SE7608223L/xx not_active Application Discontinuation
- 1976-09-08 JP JP51107651A patent/JPS5231054A/ja active Granted
- 1976-09-08 JP JP51107650A patent/JPS5239629A/ja active Pending
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