191658. lajstromszámú szabadalom • Eljárás cefém-karbonsav-származékok előállítására
1 2 191 658 5,30 (1H,D, J = 13Hz,O720C0) 5.00 (1H, D, J = 4 Hz, H6) 4,95 (1H,D,J = 13 Hz,C7/2OCO) 4.00 (3H, aromás C//2NH3+ és Ctf2SO) 3,63 (1H,D,J = 17Hz,C//2SO) 2,40 (4H,M,(g)) 2,20 (6H, S, C//3 aromás) 1,90 (2H,M,(h)). 5,40 (1H,D,J = 13H/.,C//20C0) 4,98 (1H, D, J = 4 Hz, H6) 4,79 (1H, D, J = 13 Hz, C//2OCO) 4.05 (1H, D, J = 17 Hz, Ci/2SO) 5 3,75 (1H, D, J = 17 Hz, CH2SO) 3.06 (2H, M, OC-CH2C//2NH3+) 2,70 (2H, M, OC-C//2CH2NH3+) 1,45 (6H, 2S, (C//3)2C). SR 42 542 NMR-spektruma (96) 250 MHz-en: 5 (ppm) 8.90 (1H, D, J = 9 Hz, CON//) 7.90 (3H, S.e., CH2N//3+) 7.00 (1H, S, aromás//) 6.90 (1H,S,//tiazol) 6.00 (III, DD,J, = 9Hz,J2 = 4Hz,//7) 5.30 (1H, D, J== 13 Hz, CH2OCO) 5.00 (1H, D, J = 4 Hz,i/6) 4.94 (1H,D, J = 13Hz,C/72OCO) 4.00 (3H, M, aromás C/72NH3+ és C//2SO) 3,62 (1H,D,J = 17Hz,C//2SO) 2,50 (4H, M, (g)) 2,32 (3H, S, aromás C//3) 2,20 (3H, S, aromás C//3) 2,16 (3H, S, aromás CH3) 1.90 (2H,M,(h)). SR 42 544 NMR-spektruma (97) 250 MHz-en: ő (ppm) 10,30 (1H,S, aromás N//CO) 8.70 (1H, D, J = 9 Hz, CON//) 8.30 (1H, S.e., aromásH 2'-helyzetben) 8.05 (3H, M, CHjNZ/a4) 7.70 (2H, M, aromás H 5'- és ó'-helyzetben) 6.95 (1H, S, 7/ tiazol) 6.00 (1H, DD, Jj = 9 Hz, J2= 4 Hz,//7) 5.45 (1H, D, J = 13 Hz, C//2OCO) 4.03 (1H,D,J = 17Hz,C//2SO) 3,85 (2H, M, C//2NH3+) 3.75 (1H, D, J = 17 Hz, Ci/2SO) 1,47 (6H, 2S,(C//3)2C). SR 42 545 NMR-spektruma (98) 250 MHz-en: ő (ppm) 9.90 (1H,S, aromás N//CO) 8,66 (1H, D, J = 9 Hz, CON//) 8,28 (1H, S, aromás H 2'-helyzetben) 7.70 (5H,M, aromás H 5'- és ó’-helyzetben és CH2N//3+) 6.95 (1H,S, H tiazol) 6.00 (1H, DD,J1 = 9Hz,J2 = 4Hz,T/7) 5.45 (1H, D, J = 13 Hz, C//2OCO) 5.00 (1H, D, J = 4 Hz, H6) 4,84 (1 H, D, J = J 3 Hz, C//2OCO) 4.03 (1H, D, J = 17 Hz, CH2SO) 3,68 (1H, D, J = 17 Hz, CH2SO) 3.05 (2H, M,COCH2C//2NHj+) 2.75 ,(2H, T„ J = 7 Hz, CO^CHjNHs^ 1.46 (6H, 2S, (Cff3)2C). SR 42 547 NMR-spektruma (100) 250 MHz-en: 5 (ppm) 12,75 (1H, S.e., tiazol N//CO) 8.90 (1H, D, J = 9 Hz, CON77) 8.15 (4H, M, CH2N//3+ és tiazol 3-77-je) 6.96 (1H, S, H tiazol) 6.00 (1H, DD, Ji = 9 Hz, J2 = 4 Hz,T/7) 5.40 (1H, D, J = 13 Hz, C//2OCO) 4,98 (1H,D,J = 4Hz,^6) 4.81 (1H, D, J = 13 Hz,Ci/20C0) 4.00 (1H, D, J = 17 Hz, Ci/2SO) 3,86 (2H,M,a/2NH3^ 3,66 (1H, D, J = 17 Hz, CH2SÖ) 2,50 (4H,M,(g)) 1.90 (2H,M,(h)). SR 42 548 NMR-spektruma (101) 250 MHz-en: Ô (ppm) 10,80 (1H, S, aromás N//CO) 8,95 (1H, D, J = 9 Hz, CÖN//) 8.15 (3H,S.e.,CH2NH3+) 7.90 (2H, D, I = 8 Hz, aromás H 2'- és 6'-lielyzetben) 7,70 (2H, D, J = 8 Hz, aromást 3'- és 5'-helyzetben) 6.97 (1H, S, H tiazol) 6.00 (1H, DD, Ji = 9 Hz, J2 = 4 Hz, //7) 5,36 (1H, D,»J = 13 Hz, C//2OCO) 5.00 (lH,D,J = 4Hz,H6) 4.82 (1H, D, J = 13 Hz, CH2OCO)' 4.05 (1H,D,J = 17Hz,Œ2SO) 3.80 (3H, M, C/72NH3+ és CH2SO) 2.40 (2H, M, (g)) 1.90 (2H, M, (h)). SR 42 549 NMR-spektruma (102) 250 MHz-en: 5 (ppm) 8.45 (1H, D, J = 9 Hz, CON/f) 8.00 (3H,S.e.,CH2N/73+) 6,79 (1H, S, H tiazol) 5.98 (1H, DD, Jj = 9 Hz, J2= 4 Hz,Hn~) 5.15 (HI, 2D, J = 13 Hz, CH2OCO) 4,97 (1H, D, J = 4Hz,//6) 4,62 (1H, D, J = 13 Hz, CH2OCO) 4.15 (1H, D.e., J = 12 Hz, piperidin ekvatoriális H2) 3.84 (3H, M, C//2NH3+) és Ctf2SO) 3,58 (2H, M, CH2SO és piperidin ekvatoriális H6) 3.05 (1H, T.e., J = 12 Hz, piperidin axiális//2) 2.81 (1H, T.e., J = 12 Hz, piperidin axiális//6) 1.84 (2H, M, piperidin H2 és Hs) 1 ^0 (2H, M, piperidin H3 ésHs) 1.45 (6H, 2D, (C//3)2C). 10 15 20 25 30 35 40 45 50 55 SR 42 546 NMR-spektruma (99) 250 MHz-en: 8 (ppm) 10,5 (1H, S, aromás N//CO) 8,56 (1H, D, J = 9 Hz, CON//) 7,89 (2H, D, J = 8 Hz, aromás H 2'- és 6'-helyzetben) 7.70 (2H, D, J = 8 Hz, aromás H 3'- és 5'-helyzetben) 7.70 (3H,S.e.,(CH2)2Ntf3+) 6,95 (1H.S,//tiazol) 5,98 (1H,DD,Ji = 9Hz,J2 = 4Hz,//7) SR42 581 NMR-spektruma (103) 250 MHz-en: 5 (ppm) 8,72 (1H, D, J = 9 Hz, CON//) 8,25 (3H, S.e., CH2N//3+) 7,75 (3H, M, aromás H) 6,97 (1H, S, H tiazol) 6.00 (1H, DD, Jj= 9 Hz, J2 = 4 Hz,//7) 5,45 (1H, D, J = 13 Hz, C//2OCO) 5.00 (1H, D, J = 4 Hz,//6) 31
