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US4003922A
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Synthesis of cis-1,4-cyclohexadiene dioxide
Assignee: Bristol Myers Co
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Filing: 1976-02-10
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Granted: 1977-01-18
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Expires: 1996-02-10
Abstract
Abstract Cis-1,4-cyclohexadiene dioxide is a valuable intermediate useful in the preparation of totally synthetic aminoglycosides. An example of such an aminoglycoside is 5-deoxykanamycin A.
Inventors
- 👤 Gerry Kavadias
- 👤 Bernard Belleau
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 21:07
CPC Classifications
C; C07; C07H; C07H17/00; C07D; C07D231/00; C07D231/54; C07D263/00; C07D263/52; C07D263/54; C07D263/58; C07D493/00; C07D493/02; C07D493/04; C07H15/00; C07H15/20; C07H15/22; C07H15/222; C07H15/224; C07H15/226; C07H15/234
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
56 words
A process for the preparation of the compound having the formula ##STR18##which process comprises the oxidizing of 1,4-cyclohexadiene with m-chloroperbenzoic acid in a temperature range of about -10° C. to about +35 ° C to produce a mixture of cis-and trans- bisepoxides in a ratio of about 2:1, respectively, and separating the cisbisepoxide from the mixture.
Claim 2
Dependent Claim
56 words
A process for the preparation of the compound having the formula ##STR18##which process comprises the oxidizing of 1,4-cyclohexadiene with m-chloroperbenzoic acid in a temperature range of about -10° C. to about +35 ° C to produce a mixture of cis-and trans- bisepoxides in a ratio of about 2:1, respectively, and separating the cisbisepoxide from the mixture.
Claim 3
Dependent Claim
61 words
A process of claim 1 for the preparation of cis-1,4-cyclohexadiene dioxide wherein the oxidation is conducted wtih a ratio of about 1 mole of diene per two to three moles of peracid in a reaction inert organic solvent selected from the group consisting of methylene chloride, dichloroethane, chloroform, benzene, hexane, toluene, diethylether and dioxane with stirring for at least 3 hours.
Claim 4
Dependent Claim
46 words
The process of claim 2 for the preparation of cis-1,4-cyclohexadiene dioxide wherein the oxidation is conducted with a ratio of about 1 mole of diene per two moles of m-chloroperbenzoic acid at about 0° C. to about +10° C. for at least 3 hours with stirring.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-18 | 1980-07-19 | 1981-01-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-18 | 1984-07-19 | 1985-01-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-18 | 1988-07-19 | 1989-01-18 | $7700.00 | Window Closed / Lapsed |