Preparation of penem derivatives and azetidinone intermediates

Details Preparation of penem derivatives and azetidinone intermediates Preparation of penem derivatives and azetidinone intermediates

1983-06-10

1986-06-17

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

544364, 544368, 2602452R, 544405, 544406, 2602454, 544407, 544408, 2603303, 546193, 546194, 2603309, 546198, 546208, 544 3, 546256, 546270, 544 54, 546275, 560186, 544 582, 544 584, 544 585, 544 586, 544 587, 544 63, 544 96, 544 98, 544111, 544238, 544310, 544312, 544316, 544317, 544319, 544320, 544321, 544322, 544326, 544328, 544331, 544332, 544333, 544335, 544336, 544359, C07D20508, C07D49804, C07D40312, C07D40112

Patent

active

045955395

ABSTRACT:
Certain 2-substituted-2-penem-3-carboxylic acid compounds and pharmaceutically-acceptable salts thereof can be prepared from the appropriate xanthate or trithiocarbonate by desulfurization and addition of an electrophilic sulfur compound followed by halogenation and ring closure. The corresponding desulfurized and halogenated olefinic intermediates are disclosed.

REFERENCES:
patent: 3668201 (1972-06-01), Gutanski
patent: 3960940 (1976-06-01), Elks
patent: 4008229 (1977-02-01), Spitzer
patent: 4020077 (1977-04-01), Cook
patent: 4155912 (1979-05-01), Menard et al.
patent: 4168314 (1979-09-01), Christensen et al.
patent: 4207323 (1980-06-01), Beattie et al.
patent: 4272437 (1981-06-01), Menard et al.
patent: 4290948 (1981-09-01), Brain et al.
Reese et al, "Protective Groups in Organic Chemistry" (pp. 95-142) 1973.
Haines, Adv Carbohydrate Chain, 33, 11-109 (1976).
Dininno, Journal of the American Chemical Society, 101,2210-11 (1979).
Oida et al., Tetrahedron Letters, 21,619-20 (1980).
Hayashi et al., 2-(Alkylthio)penem-3-Carboxylic Acids. V., Chem. Pharm. Bull., 29(11), 3158-3172 (1981).
Yoshida et al., 2-(Alkylthio)penem-3-Carboxylic Acids. IV., Chem. Pharm. Bull., 29(10), 2899-2909 (1981).
Volante, A, New Highly Efficient Method for the Conversion of Alcohols to Thioesters and Thiols, Tetrahedron Letters, 22(33), 3119-3122 (1981).
Oida et al., 2-(Alkylthio)penem-3-Carboxylic Acids. II., Chem. Pharm. Bull., 28(11), 3258-3264 (1980).
DeNinno, et al., A Convenient Synthesis of Racemic 6-Hydroxyethyl-2-Alkylthio-Substituted Penems, Tetrahedron Letters, 28(35), 3535-38 (1982).
Tanaka et al., 2-Thioxopenams, Useful Intermediate for Penem Synthesis, Chem. Comm., 1982(13), 713-714 (1982).
J. L. Wardell, Preparation of Thiols, in The Chemistry of the Thiol Group, S. Patai, ed., John Wiley & Sons, London, 1974, Chapt. 4.
A. Afonso et al., New Synthesis of Penems, the Oxamide Cyclization Reaction, J. Amer. Chem. Soc., 104,6138-39 (1982).

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