Claims
- 1. A process for preparing a compound having the formula ##STR18## wherein R.sup.8 represents a group selected from the group consisting of straight or branched lower alkyl, lower alkoxymethyl, benzyloxymethyl, lower alkanoyloxy lower alkyl, benzoyloxymethyl, cyanomethyl, 2,2,2-trichloroethyl, phthalimidomethyl, benzyl, p-methoxybenzyl, p-nitrobenzyl, benzhydryl, phenacyl, p-bromophenacyl, p-methoxyphenacyl, p-nitrophenacyl, and tri lower alkylsilyl, R.sup.9 to R.sup.12 may be the same or different and each represents hydrogen or a group selected from the group consisting of straight or branched lower alkyl, lower alkoxy, halogen, cyano, lower alkoxycarbonyl, or R.sup.9 and R.sup.10 together and R.sup.11 and R.sup.12 together may be linked to form a ring fused with the benzene ring to which they are attached,
- n is 1 or 2 and R represents a straight or branched alkyl having from 1 to 6 carbon atoms which comprises contacting a penam compound having the formula ##STR19## wherein R.sup.8 to R.sup.12 and n have the same meanings as defined above, with a metal oxide in an inert solvent or with a quinone compound substituted with an electron attractive group thereby oxidizing said panam compound to its quinoid form, and contacting the resulting oxidation product with a lower alkanol having the formula R--OH wherein R has the same meaning as defined above, said metal oxide and said quinone compound being one which oxidizes phenol to a quinoid form without destruction of the penam nucleus.
- 2. A process according to claim 1 wherein said metal oxide is lead dioxide and said inert solvent is benzene.
- 3. The process according to claim 1, wherein said quinone compound is dichlorodicyanobenzoquinone.
- 4. The process according to claim 1, wherein the metal oxide is lead dioxide, said solvent is benzene and said lower alkanol is methanol.
- 5. The process according to claim 1, wherein R.sup.9 and R.sup.11 are each hydrogen, R.sup.10 and R.sup.12 are each tertiary butyl, and R is methyl.
- 6. The process according to claim 5, wherein the metal oxide is lead dioxide and the solvent is benzene.
- 7. The process according to claim 5, wherein the said quinone compound is dichlorodicyanobenzoquinone.
- 8. The process according to claim 1, wherein the penam compound is so contracted at a temperature of up to about 80.degree. C.
- 9. The process according to claim 1, wherein the alkanol is used in an excess of the stoichiometric amount related to the amount of the oxidation product.
- 10. The process according to claim 1, wherein the resulting oxidation product is so contacted at a temperature of from about 40.degree. C. to about 50.degree. C.
Priority Claims (1)
Number |
Date |
Country |
Kind |
48-100856 |
Sep 1973 |
JA |
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Parent Case Info
This is a division of application Ser. No. 501,245, filed Aug. 28, 1974, now U.S. Pat. No. 4,016,155.
US Referenced Citations (4)
Non-Patent Literature Citations (1)
Entry |
Cama, L.D. et al., "Substituted Penicillins and Cephalosporins" in Tetrahedron Letters" pp. 3505-3508 1/1973. |
Divisions (1)
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Number |
Date |
Country |
Parent |
501245 |
Aug 1974 |
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