JPS5748933A - Preparation of bicyclo 3.3.0 octane derivative - Google Patents
Preparation of bicyclo 3.3.0 octane derivativeInfo
- Publication number
- JPS5748933A JPS5748933A JP55124803A JP12480380A JPS5748933A JP S5748933 A JPS5748933 A JP S5748933A JP 55124803 A JP55124803 A JP 55124803A JP 12480380 A JP12480380 A JP 12480380A JP S5748933 A JPS5748933 A JP S5748933A
- Authority
- JP
- Japan
- Prior art keywords
- base
- metal salt
- derivative
- methanoprostacycline
- oxo
- 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.)
- Pending
Links
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical class CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 title abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- 239000002184 metal Substances 0.000 abstract 3
- 229910052751 metal Inorganic materials 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000006482 condensation reaction Methods 0.000 abstract 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 abstract 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000006243 carbonyl protecting group Chemical group 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 230000003449 preventive effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- -1 zinc acetate Chemical class 0.000 abstract 1
- 239000004246 zinc acetate Substances 0.000 abstract 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To prepare the titled compound useful as a synthetic intermediate of 9(O)-methanoprostacycline, etc., in a shortened production process, by the condensation reaction of diformylmethylcyclopentane derivative in the presence of a base or a base and a metal salt.
CONSTITUTION: The objective compound of formula II such as 3α-hydroxy-4β- formvl-7-oxobicyclo[3.3.0]octane, etc. is prepared by the condensation reaction of the compound of formula I (A is oxo or carbonyl-protecting group) such as 1-oxo- 3α,4α-diformyl-methylcyclopentane in a solvent such as acetonitrile in the presence of a base such as pyridine hydrochloride or a combination of the base and a metal salt such as zinc acetate, in an inert gas tream (e.g. N2) at -10°C W about room temp. for 30minW10hr. The amount of by-product can be reduced by using a metal salt in combination with the base.
USE: A synthetic intermediate of 9(O)methanoprostacycline or its derivative effective as a remedy and preventive for thermobosis.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55124803A JPS5748933A (en) | 1980-09-09 | 1980-09-09 | Preparation of bicyclo 3.3.0 octane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55124803A JPS5748933A (en) | 1980-09-09 | 1980-09-09 | Preparation of bicyclo 3.3.0 octane derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5748933A true JPS5748933A (en) | 1982-03-20 |
Family
ID=14894506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55124803A Pending JPS5748933A (en) | 1980-09-09 | 1980-09-09 | Preparation of bicyclo 3.3.0 octane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5748933A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4946467A (en) * | 1988-03-14 | 1990-08-07 | Gunze Limited | Surgical suture |
| JP2006515783A (en) * | 2003-01-27 | 2006-06-08 | セルジオ カプーリョ， | Covered surgical elastic yarn |
-
1980
- 1980-09-09 JP JP55124803A patent/JPS5748933A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4946467A (en) * | 1988-03-14 | 1990-08-07 | Gunze Limited | Surgical suture |
| JP2006515783A (en) * | 2003-01-27 | 2006-06-08 | セルジオ カプーリョ， | Covered surgical elastic yarn |
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