US4008230A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing 3-hydroxy cephalosporins
Assignee: Eli Lilly and Co
•
Filing: 1975-10-29
•
Granted: 1977-02-15
•
Expires: 1995-10-29
Abstract
Abstract 3-Hydroxycephalosporins are prepared by treating a 3-hydroxy-4-bromo-2-(2-formylthio-4-oxo-3-amido or imido-1-azetidinyl)-2-butenoate ester with mercuric acetate and contacting the resulting reaction mixture with a mercuric ion precipitator.
Inventors
- 👤 Gary A. Koppel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 18:01
CPC Classifications
C; C07; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/09; C07D205/095
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
68 words
A process for preparing a 3-hydroxycephalosporin of the formula ##STR17## which comprises the step of reacting a compound of the formula ##STR18## with mercuric acetate in an inert solvent medium, and adding a mercuric ion precipitator to the resulting reaction mixture, in which, in the above formulae, R 1 is a carboxylic acid protecting group, and R is a. phthalimido; b. an amido group of the formula ##STR19##
Claim 2
Dependent Claim
68 words
A process for preparing a 3-hydroxycephalosporin of the formula ##STR17## which comprises the step of reacting a compound of the formula ##STR18## with mercuric acetate in an inert solvent medium, and adding a mercuric ion precipitator to the resulting reaction mixture, in which, in the above formulae, R 1 is a carboxylic acid protecting group, and R is a. phthalimido; b. an amido group of the formula ##STR19##
Claim 3
Dependent Claim
22 words
in which R 2 is 1. hydrogen, C 1 --C 3 alkyl, halomethyl, thienyl-2-methyl, 4-protected-amino-4-protected carboxybutyl, benzyloxy, 4-nitrobenzyloxy, t-butyloxy, 2,2,2-trichloroethoxy, 4-methoxybenzyloxy; 2.
Claim 4
Dependent Claim
22 words
in which R 2 is 1. hydrogen, C 1 --C 3 alkyl, halomethyl, thienyl-2-methyl, 4-protected-amino-4-protected carboxybutyl, benzyloxy, 4-nitrobenzyloxy, t-butyloxy, 2,2,2-trichloroethoxy, 4-methoxybenzyloxy; 2.
Claim 5
Dependent Claim
78 words
a group of the formula R'--(O) m --CH 2 -- in which m is 0 or 1, and R' is phenyl or phenyl substituted with 1 or 2 halogens, protected hydroxy, nitro, cyano, trifluoromethyl, C 1 -C 4 alkyl, or C 1 -C 2 alkoxy; 3. a group of the formula ##STR20## in which R' is as defined above and W is protected hydroxy, protected carboxy, or protected amino; or c. an imidazolidinyl group of the formula ##STR21##
Claim 6
Dependent Claim
78 words
a group of the formula R'--(O) m --CH 2 -- in which m is 0 or 1, and R' is phenyl or phenyl substituted with 1 or 2 halogens, protected hydroxy, nitro, cyano, trifluoromethyl, C 1 -C 4 alkyl, or C 1 -C 2 alkoxy; 3. a group of the formula ##STR20## in which R' is as defined above and W is protected hydroxy, protected carboxy, or protected amino; or c. an imidazolidinyl group of the formula ##STR21##
Claim 7
Dependent Claim
38 words
in which R' is as defined above. 2. Process of claim 1, in which R 1 is C 4 -C 6 tert-alkyl, 2,2,2-trihaloethyl, 2-iodoethyl, benzyl, p-nitrobenzyl, succinimidomethyl, phthalimidomethyl, p-methoxybenzyl, benzhydryl, C 2 -C 6 alkanoyloxymethyl, phenacyl, or p-halophenacyl.
Claim 8
Dependent Claim
16 words
Process of claim 2, in which R 1 is t-butyl, benzyl, p-nitrobenzyl, p-methoxybenzyl, benzhydryl, or 2,2,2-trichloroethyl.
Claim 9
Dependent Claim
15 words
Process of claim 1, in which R is an amido group of the formula ##STR22##
Claim 10
Dependent Claim
19 words
Process of claim 4, in which R 2 is a group of the formula R'--(O) m --CH 2 --.
Claim 11
Dependent Claim
9 words
Process of claim 5, in which R' is phenyl.
Claim 12
Dependent Claim
15 words
Process of claim 4, in which R 2 is a group of the formula ##STR23##
Claim 13
Dependent Claim
31 words
Process of claim 1, in which the reaction is carried out in the presence of a mixture of an aprotic inert organic solvent and a C 1 -C 4 carboxylic acid.
Claim 14
Dependent Claim
16 words
Process of claim 8, in which the C 1 -C 4 carboxylic acid is acetic acid.
Claim 15
Dependent Claim
23 words
Process of claim 1, in which the reaction is carried out at a temperature of from about -10° C. to about +25° C.
Claim 16
Dependent Claim
13 words
Process of claim 1, in which the mercuric ion precipitator is hydrogen sulfide.
References Cited (Backward Citations)
US3917588A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-02-15 | 1980-08-16 | 1981-02-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-15 | 1984-08-16 | 1985-02-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-15 | 1988-08-16 | 1989-02-15 | $7700.00 | Window Closed / Lapsed |