Electrolysis: processes – compositions used therein – and methods – Electrolytic synthesis – Preparing organic compound
Patent
1995-12-08
1997-08-26
Gorgos, Kathryn L.
Electrolysis: processes, compositions used therein, and methods
Electrolytic synthesis
Preparing organic compound
205426, 205431, 205435, 205437, 205441, 205443, 205445, 205455, 205456, 540215, C25B 300
Patent
active
056607113
ABSTRACT:
A process is described for preparing 3-exomethylene cephalosporanic acid derivatives for use in the synthesis of cephalosporin antibiotics such as ceftibuten. The process comprises electrochemical reduction of a compound of the formula (IV) ##STR1## wherein: R.sup.3 is CH.sub.3 C(O)--; ##STR2## is an optional sulfoxide group; n is 2 or 3; R.sup.1 is H and R is H or NHR.sup.2, where R.sup.2 is H or a protecting group selected from C.sub.6 H.sub.5 CH.sub.2 OC(O)--, C.sub.6 H.sub.5 C(O)-- or C.sub.1 -C.sub.6 alkoxy-C(O)--; or wherein R and R.sup.1 together with the carbon atom to which they are attached comprise --C(O)--, and produces the desired 3-exomethylene compounds with low levels of the corresponding 3-methyl tautomers.
REFERENCES:
patent: 3792995 (1974-02-01), Ochiai et al.
patent: 4008228 (1977-02-01), Chauvette
patent: 4042472 (1977-08-01), Hall
patent: 4224415 (1980-09-01), Meitzner et al.
patent: 4297220 (1981-10-01), Meitzner et al.
patent: 4379739 (1983-04-01), Hall
patent: 4634697 (1987-01-01), Hamashima
Ochiai et al., "Electrochemical Reduction of cephalosporanic Acids", J. Chem. Soc., Perkins Trans., pp. 258-262. ? 1974.
Yoshioka, Pure Appl. Chem., 59, 1041-1046 (1987) No month available.
Jones et al., J. Pharm. Pharmac., 20 (Suppl.), 45S-47S (1968) No month available.
Hall J. Pharm. Sci., 62 (6), 980-983 (1973).
Ochiai et al., J. Chem. Soc., Perkins Trans. I, 258-262 (1974) No month available.
Baldwin et al., Tetrahedron, 49 (22), 4907-4922 (1993) No month available.
Torii et al., Bull. Chem. Soc. Jpn., 59, 3975-3976 (1986) No month available.
Torii et al., Bull. Soc. Chim Belg., 91 (12), 951-965 (1982) No month available.
Hamashima et al., J. Antiobiot., 40(10), 1468-1470 (1987) No month available.
Ochiai et al., Tet. Lett., (23) 2341-2344 (1972) No month available.
Hall et al., J. Electranal. Chem., 80, 155-170 (1977) No month available.
"Kirk-Othmer Concise Encyclopedia of Chemical Technology", John Wiley & Sons, New York, 843-844 (1985) No month available.
Walker, et al., J.C.S. Perkin I, 2030 (1975) No month available.
Chemical Abstracts, vol. 122 No. 17 (Apr. 24 1995), abstract No. 213854f.
Bernasconi Ermanno
Lee Junning
Martin Charles R.
Menon Vinod Parakkal
Sogli Loris
Blasdale John H. C.
Gorgos Kathryn L.
Majka Joseph T.
Schering Corporation
Thompson Paul A.
LandOfFree
Process for the preparation of intermediates useful in the synth does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of intermediates useful in the synth, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of intermediates useful in the synth will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1985540