Reference

Azetidinephosphorothioates

Azetidinephosphorothioates. Zahler, Robert; Koster, William H. (Squibb, E.In this study， 72229-74-4 and 80542-76-3 are also used. R., and Sons, Inc. , USA). Eur. Pat. Appl. EP 95394 A2 30 Nov 1983, 32 pp. DESIGNATED STATES: R: AT, BE, CH, DE, FR, GB, IT, LI, LU, NL, SE. (English). (European Patent Organization). CODEN: EPXXDW. CLASS: IC: C07F009-65; A61K031-675. APPLICATION: EP 83-400750 15 Apr 1983. PRIORITY: US 82-381260 24 May 1982. DOCUMENT TYPE: Patent CA Section: 29 (Organometallic and Organometalloidal Compounds) Section cross-reference(s): 28, 63 Title compds. I (R = OH, alkoxy, aryloxy, alkyl, aryl, amino, alkylthio, arylthio; R1, R3, R4 = H, alkyl, aryl; R2 = H, MeO) were prepd. The trifluoroacetic acid salt of (S)-(3-amino-2-oxo-1-azetidinyl)thiophosphoric acid Et ester was treated with the mixed anhydride of di-Ph chlorophosphate with (Z)-2-amino-a-[[2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy]imino]-4 -thiazoleacetic acid to give a product which was purified by chromatog. on Dowex 50X2-400 (K+ form) to give 3S(Z)-I (R = OEt, R1 = benzhydryl, R2-R4 = H), which was hydrolyzed to give 3S(Z)-I (R = OEt, R1 = K, R2-R4 = H). Similarly prepd. were 3S(Z)-I (R = OH, R1-R4 = H; R = PrNH, R1 = K, R2-R4 = H). Bactericidal I may be administered to mammals at 1.4-350 mg/kg/day. .

Regioselective Activation of Aminothiazole(iminoxyacetic acid)acetic Acid: An Efficient Synthesis of the Monobactam Aztreonam

Regioselective Activation of Aminothiazole(iminoxyacetic acid)acetic Acid: An Efficient Synthesis of the Monobactam Aztreonam. Singh, Janak; Denzel, Theodor W.; Fox, Rita; Kissick, Thomas P.; Herter, Rolf; Wurdinger, Joseph; Schierling, Peter; Papaioannou, Chris G.; Moniot, Jerome L.; Mueller, Richard H.; Cimarusti, Christopher M. ( Process Research and Development, Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, NJ 08543, USA). Organic Process Research & Development, 6(6), 863-868 (English) 2002 American Chemical Society. CODEN: OPRDFK. ISSN: 1083-6160. DOCUMENT TYPE: Journal CA Section: 26 (Biomolecules and Their Synthetic Analogs) An efficient synthesis of the monobactam aztreonam [[2S- [2a,3b(Z)]]-3[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]ac etyl]amino]-2-methyl-4-oxo-1-azetidinesulfonic acid] by acylation of an a-aminoazetidinone with the regioselectively activated aminothiazoleiminoxyacetic diacids is described. Reaction of a benzhydryl ester with N-hydroxybenzotriazole and dicyclohexylcarbodiimide followed by ester deprotection formed the monoacid amide. Alternatively, chemoselective transient silylation of the a diacid followed by activation with N-hydroxysuccinimide formed active ester.Several substances like 80542-76-3 may be metioned in this study. Acylation of an a-aminoazetidinone with amide or ester produced aztreonam in 75-85% yield. .