191658. lajstromszámú szabadalom • Eljárás cefém-karbonsav-származékok előállítására

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3,94 (1H, D, J = 17 Hz, CH2SO)

3,89 (1H, D, J=17 Hz, C//2SO)

3,55 (1H,D, J=17 Hz, C/72SO)

3,52 (1H, D,J = 17Hz,C//2SO)

1,44 (6H, S, (C//3)2C)

3,20 (2H, M, C//2CH)

1,14 (3H, D, J = 7 Hz, C//3CH).

1,44 (6H, S, (CH3)2C). 5

SR 41 886 NMR-spektruma ( 16) 250 MHz-en: 5 (ppm)

8,50

(1H, D, J=9 Hz, CON//)

8,40

(3H, S.e.. N//3+)

7,66

(1H,S,C0N#2)

7,50

(3H, S.e.. N773+)

7,22

(1 H, S, CO N/72)

6,78

(1H,S,//tiazol)

6,00

(1H, DD, J j = 9 Hz, J2 = 4 Hz, H2)

5,29

(1H, D, J = 13 Hz, CH2OCO)

4,92

(1H,D,J=4Hz ,H6)

4,79

(1H, D, J = 13 Hz, C//2OCO)

4,26

(1H,M,C//NH2)

3,92

(1H, D, J = 17 Hz, C//2SO)

3,52

(lH,D,J = 17Hz,C//2SO)

2,71

(2H, M, C//2CONH2)

1,44

(6H, S, (C//3)2C).

10

15

20

SR 41 887 NMR-spektruma (17) 250 MHz-en: 5 (ppm)

8.50 (1H, D, J-9 Hz, CON//)

8.45 (3H, S.e., N//3+)

7.45 (3H, S.e., NH3+)

6.78 (1H, S,H tiazol)

6.00 (1 H, DD, J1 = 9 Hz, J2 = 4 Hz,//7)

5.24 (1H, D, J= 13 Hz, C//2OCO)

4,98 (1H,D,J=4Hz,//6)

4.82 (1H, D, J = 13 Hz, CH2OCO)

4,13 (1H, M, C//NH2)

3.92 (1H,D, J=17Hz,O72S0)

3,10 (1H, D, J= 17 Hz, C//2SO)

2.50 (1H,M,C//2S)

2.00 (5H, M, CH3S és Ctf2-CH2-S)

1,44 (6H, S, (C//3)2C).

SR 41 888 NMR-spektruma (18) 250 MHz-en: 5 (ppm)

8.50 (4H,M,C0N//,N//3+)

7,80 (3H,S.e.,N7/3+)

7.50 (3H, S.e., N//3+)

6.79 (1H, S,H tiazoi)

6.00 (1H, DD, Ji = 9 Hz, J2 = 4 Hz,#7)

5.24 (1H, D, J = 13 Hz, CH2OCO)

4.97 (lH,D,J = 4Hz,tf6)

4.82 (111, D, J = 13 Hz, CH2OCO)

3.97 (1H, M, C7TNH2)

3.92 (1H, D, J = 17 Hz, C//2SO)

3,60 (1H, D. J = 17 Hz, CH2SO)

2.75 (2H, M, C//jNH2)

1.75 (1H, M, CH2CU)

1,40 (11H, S.e., (CH&C, (C//2)3CH2NH2).

25

30

35

SR 41 889 NMR-spektruma (19) 250 MHz-en: 6 (ppm)

9.00 (1H, S, H2 imidazol)

8,60 (3H, S.e., N//3+)

8,50 (1H, D, J=9 Hz, CON//)

7.40 (lH, S,tf4 imidazol)

7,30 (3H, S.e., N//3+)

6,79 (1H,S, H tiazol)

6.00 (1H, DD, J1 =9 Hz, J2=4 Hz,//7)

5,22 (1H, D, J= 13 Hz, C//2OCO)

4,97 (1H,D, J=4Hz,//6)

4,90 (1H, D, J= 13 Hz, C//2OCO)

4.40 (1H, M, C77NH2)

SR 41 891 NMR-spektruma (20) 250 MHz-en: 8 (ppm)

8.50 (1H, D, J = 9 Hz, CON//)

8.40 (3H, S.e., N//3+)

7.40 (3H, S.e., Ni/3+)

6,77 (1H,S, H tiazol)

6.00 (1H,DD,J, = 9Hz,J2 = 4Hz,Hn)

5,76 (1H, D, J = 13 Hz, CH2OCO)

4.95 (lH,D,J=4Hz,i/6)

4,81 (1H, Dí J = 13 Hz, Ci/2OCO)

4,06 (1H,M,C//NH2)

3.95 (1H, D, J = 17 Hz, C//2SO)

3,63 (lH,D,J = 17Hz,Ctf2SO)

1.44 (6H, S, (C//3)2C)

1,36 (3H,D,J=7Hz,C//3CH).

SR 41 967 NMR-spektruma (21) 60 MHz-en: S (ppm)

6,5-9,0 (8H, széles jel, Ntf2, C02//, TFA)

8.35 (1H,D, J = 9 Hz.CONTT)

6.80 (lH,S,/7 tiazol)

6.00 (1H, DD, J j = 9 Hz, J2 = 4 Hz, //7)

5,15 (1H, AB A-ja, JAB= 13 Hz,C//2OCO)

5.00 (1H,D,J=4Hz,//6)

4.65 (1H, AB B-je, JAB=13 Hz, CH2OCO)

3.95 (1H, AB A-ja,JAB=17Hz, C//2SO)

3.65 (1H, ABB-je, JAB=17Hz, Œ2SO)

2.80 (2H, M, C//2NH2)

2.35 (2H, M, C//2CO)

1.45 (10H, S.e., (C//3)2C és CH2(C7/2)2CH2).

SP 41 975 NMR-spektruma (22) 60 MHz-en: 8 (ppm)

6— 9 (8H, széles jel, TFA, N772, C02/7)

8,42 (1 H, D, J=9 Hz, CON//)

6,85 (1H,S,//tiazol)

6.05 (1H, DD, J] = 9 Hz, J2 = 4 Hz,//7)

5,30 (1H, AB A-ja, J= 13 Hz,CH2OCO)

5.05 (1H,D, J = 4 Hz,/76)

4,68 (1H, AB B-je, JAB = 13Hz, C//2OCO)

4.00 (1H, AB A-ja, JAB = 17Hz, C//2SO)

3.65 (1H, AB B-je, JAB = 17Hz, CH2SO)

1.75 (8H, M,//ciklopentán)

1.45 (ólkS.ÍO/^C).

SR 41 976 NMR-spektijimá’ (23) 60 MHz-eh: 8 (ppm)

7- 10 (8H, széles jel, TFA, N//2, CO2H)

8.50 (1H, D, J = 9 Hz, CON//)

6,92 (1H, S,H tiazol)

6.10 (lH,DD,J,=9Hz,J2 = 4Hz,//7)

5.35 (1H, AB A-ja, J=13 Hz, CH2OCO)

5.00 (1H,D,J = 4 Hz,/76)

4.75 (1H, AB B-je, J = 13 Hz, CH2OCO)

4.00 (1H, AB A-ja,JAB= 17 Hz, C/72SO)

3,70 (1H, AB B-je, JAB= 17 Hz, CH2SO)

1.00- 2,30 (16H, M, (C//3)2C és ciklohexán).

SR 41 977 NMR-spektruma (24) 60 MHz-en: 8 (ppm)

8.00- 10,00 (9H, széles jel, N//2, OH, CO 2H, TFA) 8,55 (1H, D, J = 9 Hz, CON/7)

7.10 (2H,D, J=8 Hz,H meta OH)

6,90 (1H, S,H tiazol)

6.80 (2H,D,J=8 Hz,//orto-OH)

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