DE2206849C2 - Verfahren zur Aufspaltung von 2-(2β-Benzyloxymethyl-3α-hydroxy-4-cyclopenten-1α-yl)- essigsäure - Google Patents
Verfahren zur Aufspaltung von 2-(2β-Benzyloxymethyl-3α-hydroxy-4-cyclopenten-1α-yl)- essigsäureInfo
- Publication number
- DE2206849C2 DE2206849C2 DE2206849A DE2206849A DE2206849C2 DE 2206849 C2 DE2206849 C2 DE 2206849C2 DE 2206849 A DE2206849 A DE 2206849A DE 2206849 A DE2206849 A DE 2206849A DE 2206849 C2 DE2206849 C2 DE 2206849C2
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- acetic acid
- benzyloxymethyl
- chloroform
- cyclopentene
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical class C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- 150000003180 prostaglandins Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- -1 PGE 1 Chemical class 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12031571A | 1971-03-02 | 1971-03-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2206849A1 DE2206849A1 (de) | 1972-12-21 |
| DE2206849C2 true DE2206849C2 (de) | 1982-09-23 |
Family
ID=22389512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2206849A Expired DE2206849C2 (de) | 1971-03-02 | 1972-02-14 | Verfahren zur Aufspaltung von 2-(2β-Benzyloxymethyl-3α-hydroxy-4-cyclopenten-1α-yl)- essigsäure |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3766264A (enExample) |
| JP (1) | JPS5246945B1 (enExample) |
| BE (1) | BE779164A (enExample) |
| CH (1) | CH547241A (enExample) |
| DE (1) | DE2206849C2 (enExample) |
| FR (1) | FR2128323B1 (enExample) |
| GB (1) | GB1346658A (enExample) |
| IT (1) | IT947700B (enExample) |
| NL (1) | NL160233C (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873605A (en) * | 1971-10-13 | 1975-03-25 | Pfizer | Resolution of an important prostaglandin intermediate |
| IT1164319B (it) * | 1983-07-27 | 1987-04-08 | Blaschim Spa | Procedimento per la risoluzione dell'acido (+-)2-(6'-metossi-2'-naftil)-propionico |
-
1971
- 1971-03-02 US US00120315A patent/US3766264A/en not_active Expired - Lifetime
- 1971-07-15 GB GB3336871A patent/GB1346658A/en not_active Expired
-
1972
- 1972-02-09 FR FR7204336A patent/FR2128323B1/fr not_active Expired
- 1972-02-10 BE BE779164A patent/BE779164A/xx not_active IP Right Cessation
- 1972-02-11 NL NL7201817.A patent/NL160233C/xx not_active IP Right Cessation
- 1972-02-14 DE DE2206849A patent/DE2206849C2/de not_active Expired
- 1972-02-15 CH CH214672A patent/CH547241A/fr not_active IP Right Cessation
- 1972-02-16 JP JP47015712A patent/JPS5246945B1/ja active Pending
- 1972-02-18 IT IT2074572A patent/IT947700B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2206849A1 (de) | 1972-12-21 |
| GB1346658A (en) | 1974-02-13 |
| NL160233C (nl) | 1979-10-15 |
| US3766264A (en) | 1973-10-16 |
| JPS5246945B1 (enExample) | 1977-11-29 |
| NL7201817A (enExample) | 1972-09-05 |
| BE779164A (fr) | 1972-08-10 |
| FR2128323B1 (enExample) | 1975-03-21 |
| FR2128323A1 (enExample) | 1972-10-20 |
| NL160233B (nl) | 1979-05-15 |
| CH547241A (fr) | 1974-03-29 |
| IT947700B (it) | 1973-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |