US4229592A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Intermediate for prostaglandins and process for preparing the intermediate
Assignee: University of Kansas
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Filing: 1978-02-06
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Granted: 1980-10-21
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Expires: 1998-02-06
Abstract
Abstract The compound of the formula <IMAGE> has been found to be an important and practical intermediate with the proper stereo-isomerism for the preparation of numerous prostaglandin derivatives. It can easily be converted to 4 alpha -acetoxy-2-cyclopentenone by a variety of processes.
Inventors
- 👤 Lester A. Mitscher
- 👤 George W. Clark, III
- 👤 Paul B. Hudson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 21:05
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/02; C07C69/12; C07C69/14; C07C69/145; C07C45/00; C07C45/61; C07C45/65; C07C67/00; C07C67/08; C07C67/28; C07C67/293; C07B; C07B2200/00; C07B2200/07; C07C2601/00; C07C2601/06; C07C2601/10
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
1 words
4α-acetoxy-2-cyclopentenone-3-carboxyaldehyde.
Claim 2
Dependent Claim
1 words
4α-acetoxy-2-cyclopentenone-3-carboxyaldehyde.
Claim 3
Independent Claim
69 words
The method of preparing 4α-acetoxy-2-cyclopentenone-3-carboxyaldehyde consisting essentially in acetylating terrein in the 5-position with acetic anhydride and sodium acetate at a temperature below 65° C., removing the acetoxy group of the formed 5-acetylterrein with chromous chloride, acetylating the formed 5-deoxyterrein with acetic anhydride and sodium acetate and cleaving the side chain of the formed 5-deoxy-4α-acetylterrein through oxidation of the side-chain double bond to said aldehyde in the named stereoconfiguration.
Claim 4
Independent Claim
69 words
The method of preparing 4α-acetoxy-2-cyclopentenone-3-carboxyaldehyde consisting essentially in acetylating terrein in the 5-position with acetic anhydride and sodium acetate at a temperature below 65° C., removing the acetoxy group of the formed 5-acetylterrein with chromous chloride, acetylating the formed 5-deoxyterrein with acetic anhydride and sodium acetate and cleaving the side chain of the formed 5-deoxy-4α-acetylterrein through oxidation of the side-chain double bond to said aldehyde in the named stereoconfiguration.
Claim 5
Dependent Claim
30 words
The method of claim 2 wherein said oxidation is carried out in the presence of osmium tetroxide and an alkali metal periodate in the presence of an inert organic solvent.
Claim 6
Dependent Claim
11 words
The method of claim 3 wherein said inert solvent is acetone.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-21 | 1984-04-21 | 1984-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-21 | 1988-04-21 | 1988-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-21 | 1992-04-21 | 1992-10-21 | $7700.00 | Window Closed / Lapsed |