Reference

Trifluoroethyl-thio -sulfinyl or -sulfonyl acetamidocephalosporins

Trifluoroethyl-thio -sulfinyl or -sulfonyl acetamidocephalosporins. DeMarinis, Robert M. (Smithkline Corp., USA). U.S. US 3998819 21 Dec 1976, 5 pp. Division of U.S. 3,957,770. (English). (United States of America). CODEN: USXXAM. CLASS: IC: C07D501-28. NCL: 260243000C. APPLICATION: US 73-428536 26 Dec 1973.Several substances with their cas registry numbers 24209-38-9 and 57008-24-9 may be metioned in this study. DOCUMENT TYPE: Patent CA Section: 28 (Heterocyclic Compounds (More Than One Hetero Atom)) Bactericidal cephems I (R = CF3CH2S(O)nCH2CO, n = 0, 1, 2; R1 = H, R2 = AcO, R3, R4) (4 compds.) were prepd. Thus, the addn. of CF3CH2SCH2COCl (II) in acetone to a soln. of I (R = R1 = H, R2 = AcO) in acetone contg. 5% NaHCO5 cooled to -20.degree. gave I (R = CF3CH2SCH2CO, R1 = H, R2 = AcO). Similarly, treatment of I (R = R1 = H, R2 = R3) with II gave I (R = CF3CH2SCH2CO, R1 = H, R2 = R3). The addn. of dicyclohexylcarbodiimide to a soln. of I (R = H, R1 = Me3C, R2 = R4) and CF3CH2SO2CH2CO2H in THF gave I (R = CF3CH2SO2CH2CO, R1 = Me3C, R2 = R4) which was hydrolyzed to the acid. .

Cephalosporin derivatives

Cephalosporin derivatives. (Chugai Pharmaceutical Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho JP 58135892 A2 12 Aug 1983 Showa, 14 pp. (Japanese). (Japan). CODEN: JKXXAF. CLASS: IC: C07D501-20. ICA: A61K031-545. APPLICATION: JP 82-16386 5 Feb 1982.Several reagents with their cas registry numbers 24209-38-9 and 88711-42-6 are used here. DOCUMENT TYPE: Patent CA Section: 26 (Biomolecules and Their Synthetic Analogs) Thirty-two cephalosporin derivs. D-(-)-I [R, R1 = H, halo, alkoxy, alkyl, etc.; R2 = H, (un)substituted alkyl; R3 = H, HO; R4 = H, alkoxy; R5 = H, AcO, H2NCO2, heterocyclylthio, etc.] were prepd. by amidation of 2,3,4,5-R1(HO)2RC6HCONR2CONHCH(CO2H)C6H4R3-4 (II) with III (R6 = H, CO2H-protecting groups). Thus, reaction of 5 g 3,4-(HO)2C6H3CONH(CH2)3OH and 2.8 mL ClCO2CCl3 with 4.7 g D-(-)-PhCH(NH2)CO2H gave, after treating with 1-hydroxybenzotriazole, II benzotriazol-1-yl deriv. [R = R1 = R3 = H, R2 = (CH2)3OH] in THF, which was added to a mixt. of 8.8 g 7-amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid and 5.9 mL N,O-bis(trimethylsilyl)acetamide in CH2Cl2 at 5-10° under N and the whole stirred 8 h at room temp. to give, after deprotection, 2.8 g D-(-)-I [R = R1 = R3 = R4 = H, R2 = (CH2)3OH, R5 = 1-methyl-1H-tetrazol-5-ylthio]. .