Claims
- 1. A process for preparing an azetidinone disulfide compound of the following formula: ##STR28## which comprises reacting at a temperature between about 0.degree. C. and about 30.degree. C. a 2.alpha.-alkoxy cephalosporin ester compound of the formula ##STR29## with between about 0.8 to about 1.2 equivalents of phenylsulfenyl chloride or a monosubstituted phenylsulfenyl chloride, wherein the substituent is selected from the group consisting of chloro, methoxy, methyl and acetoxy, per equivalent of the 2.alpha.-alkoxy cephalosporin ester in an aromatic hydrocarbon or chlorinated hydrocarbon solvent,
- wherein the above formulae R.sub.1 is an acyl group of the formula ##STR30## wherein R' is (a) C.sub.1 -C.sub.7 alkyl, cyanomethyl, C.sub.1 -C.sub.6 haloalkyl, 4-protected amino-4-protected carboxybutyl; or
- (b) C.sub.1 -C.sub.6 alkoxy, phenoxy, benzyloxy or 4-methoxybenzyloxy; or
- (c) the group --R" wherein R" is phenyl or substituted phenyl wherein the substituents are 1 or 2 halogens, protected hydroxy, cyano, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, protected carboxy, protected carboxymethyl, protected hydroxymethyl or protected aminomethyl; or
- (d) an arylalkyl group of the formula
- R"--(O).sub.m --CH.sub.2
- wherein m is 0 or 1; or
- (e) a substituted arylalkyl group of the formula ##STR31## wherein R'" is R" as defined above, 2-thienyl, 3-thienyl, 2-furyl or 3-furyl; W is protected hydroxy, protected carboxy, protected amino, or
- (f) a heteroarylmethyl group of the formula
- R""--CH.sub.2 --
- wherein R"" is 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-thiazolyl, 5-tetrazolyl, 1-tetrazolyl; R.sub.2 is a carboxy protecting group, R.sub.3 is phenyl or a mono substituted phenyl group where the substituents are chloro, methoxy, methyl or acetoxy and R.sub.4 is methyl, ethyl or isopropyl.
- 2. The process of claim 1 wherein R.sub.2 is diphenylmethyl, tert-butyl, p-methoxybenzyl, 2,4,6-trimethylbenzyl, trityl, 4-methoxytrityl, 4,4'-dimethoxytrityl, 4,4',4"-trimethoxytrityl.
- 3. The process of claim 1 wherein R.sub.3 is phenyl or p-methylphenyl.
- 4. The process of claim 1 wherein R.sub.1 is an acyl group of the formula ##STR32## wherein R' is (a) C.sub.1 -C.sub.7 alkyl, cyanomethyl;
- (b) C.sub.1 -C.sub.6 alkoxy
- (c) benzyl, 1-phenoxymethyl, 1-p-methoxyphenylmethyl
- (d) 2-thienylmethyl, 3-thienylmethyl 2-furylmethyl, 3-furylmethyl, 2-thiazolylmethyl, 5-tetrazolylmethyl;
- (e) 1-protected hydroxy-1-phenylmethyl, 1-protected amino-1-phenylmethyl, 1-protected amino-1-(4-protected hydroxyphenyl)methyl.
- 5. The process of claim 4 wherein R.sub.3 is phenyl or p-methylphenyl.
- 6. The process of claim 5 wherein R.sub.2 is diphenylmethyl, tert-butyl, p-methoxybenzyl, 2,4,6-trimethylbenzyl, trityl, 4-methoxytrityl, 4,4'-dimethoxytrityl and 4,4',4"-trimethoxytrityl.
- 7. The process of claim 6 wherein R.sub.2 is diphenylmethyl.
- 8. The process of claim 1 wherein R.sub.1 is an arylalkyl acyl group of the formula ##STR33## wherein R" is phenyl or substituted phenyl wherein the substituents are 1 or 2 halogens, protected hydroxy, cyano, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, protected carboxy, protected carboxymethyl, protected hydroxymethyl or protected aminomethyl; and m is 0 or 1.
- 9. The process of claim 8 wherein R.sub.3 is phenyl or p-methylphenyl.
- 10. The process of claim 9 wherein R.sub.2 is diphenylmethyl, tert-butyl, p-methoxybenzyl, 2,4,6-trimethylbenzyl, trityl, 4-methoxytrityl, 4,4'-dimethoxytrityl, 4,4',4"-trimethoxytrityl.
- 11. The process of claim 10 wherein R.sub.1 is benzoyl.
- 12. The process of claim 11 wherein R.sub.2 is diphenylmethyl.
- 13. The process of claim 12 wherein R.sub.3 is phenyl.
- 14. The process of claim 12 wherein R.sub.3 is p-methylphenyl.
Parent Case Info
This application is a division of Ser. No. 137,861 filed Apr. 7, 1980, now U.S. Pat. No. 4,302,391.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4302391 |
Kukolja |
Nov 1981 |
|
Non-Patent Literature Citations (2)
Entry |
Pfeil et al., J. Organic Chem. 46, 827, (1981). |
Gordon et al., Chem. Abs. 88, 121082d, (1977). |
Divisions (1)
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Number |
Date |
Country |
Parent |
137861 |
Apr 1980 |
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