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

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191 658

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1.70 (2H, M, CH2C//2CH2)

1,42 (6H,S,(Cff3)jC).

SR 42 029 NMR-spektruma (33) 60 MHz-en: 5 (ppm)

7.00- 9,50 (7H, N//2, N//, CO2H, TFA)

8.46 (lH,D,J = 9Hz,CON/Z)

6.90 (1H,S,//tiazol)

6.05 (1H, DD, 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)

4.70 (1H, AB B-je, JAB = 13 Hz, CH2OCO)

3.90 (1H, AB A-ja, JAB = 17 Hz, CH2SO)

3.65 (1H, AB B-je, JAB = 17 Hz, C//2SO)

2,75 (2H,M, C//2NHCH3)

2.45 (5H, M, CH3Ml és CH2CO)

1.45 (10H, S.e., (0/3)2C és CH2(0/2)2CH2).

SR 42 031 NMR-spektruma (34) 60 MHz-en: 5 (ppm)

6.00- 9,00 (8H, kiszélesedett jel, N//2, TFA, OH, CO 2fí)

8.47 (111, D, J = 9 Hz, CON//)

6.90 (1H, S,// tiazol)

6.15 (1H,DD,J1 = 9Hz,J2 = 4Hz,//7)

5.35 (1H, AB, JAB = 13 Hz,C//2OCO)

5.00 (1H, D, J -4 Hz,H6)

4.85 (1H, AB B-je, JAB = 13 Hz, CZ/2OCO)

3,95 (4H, M, CH2SO és O/OH C//NH2)

1.45 (6H, S, (C//3)2C)

1,20 (3H,D,J = 7Hz,C//3CHOH).

SR 42 042 NMR-spektruma (35) 250 MHz-en: 5 (ppm)

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

8.35 (3H, S.e., N//3+)

7.94 (2H, D, J = 8 Hz,//orto CO)

7.55 (2H, D, J=8 Hz,// méta CO)

6,84 (1H, S,// tiazol)

6.00 (1II, DD, Jj = 9 Hz, J2 = 4 Hz,//7)

5.44 (1H, D, J = 13 Hz, C//20C0)

4,99 (1H,D,J=4Hz,//6)

4.86 (1H, D, J= 13 Hz, C//2OCO)

4,10 (3H, M, C//2NH2, C//2SO)

3,72 (1H, D, J=17 Hz,C//2SO)

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

SR 42 073 NMR-spektruma (36) 60 MHz-en: 5 (ppm)

9.30 (3H, S.e., N//3+)

8.55 (1H, D, J=9 Hz, CON//)

8.05 (3H, S.e., N//3+)

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

6.05 (111, DD, J, = 9 Hz, J2 = 4 Ilz,//7)

5.30 (111, AB A-ja, JAB = 13 Hz, C//2OCO)

5.05 (1H, D, J = 4 Hz,//6)

4.70 (1H, AB B-je. JAB = 13 Hz, C//2OCO)

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

3.65 (1H, AB B-je, JAB = 17 Hz,C//2SO)

3.00 (2H, S.e., C//2NH2)

1.45 (6H, S, (C//3)2C—ON)

1,17 (6H, S, (C//3)2C02CH2).

SR 42 117 NMR-spektruma (37) 250 MHz-en: 6 (ppm)

5.00- 9,00 (8H, széles jel, CO 2H, TFA, N H2)

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

6.90 (111, S,// tiazol)

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

5.15 (1H, D, J = 13 Hz, C//2OCO)

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

4.58 (1H, D, J = 13 Hz, C//2OCO)

3.90 (1H, D, J= 17 Hz, C//2SO)

3,54 (1H,D,J = 17Hz,C//2SO)

2.60 (2H,M,C//2NH2)

2.25 (1H, T, J= 12 Hz, C//C02)

1.84 (4H, M, C//2CHCO)

1,45 (6H, S, (C//3)2C) .

1.25 (3H, M, C//CH2NH2 és C//2CHCH2NH2)

0,95 (2H, M, C//2CHCH2NH2).

SR 42 120 NMR-spektruma (38) 250 MHz-en: ő (ppm)

8,37 (1H, D, J=9 Hz, CON//)

7.90 (3H, S.e., N/Zs^

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

6.79 (1H, S,//tiazol)

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

5,11 (1H, 2D, J= 13 Hz, CH2OCO)*

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

4.61 (1H, 2D, J = 13 Hz, CH2OCO)*

3.90 (1H, D, J= 17 Hz, C//2SO)

3.59 (1H, D, J = 17 Hz, Ci/2SO)

3.00 (1H, S.e., C//NH2)

2.40 (1H,M,C//C02)

2,10 (1H,M„C//2CHNH2)

1.80 (3H, M, C//2CHNH2)

1.44 (6H, 2S, (C/Z3)2C)

1.00- 1,50 (4H, M, C/Z2-C//2-CH-C02).

SR 42 121 NMR-spektruma (39) 250 MHz-en: ô (ppm)

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

7.00- 8,00 (6H, széles jel, N//2, TFA)

6.81 (1H, S,H tiazol)

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

5,15 (1H, 2D, J = 13 Hz, CH2OCO)*

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

4,63 (1H, 2D, J = 13 Hz, C//2OCO)*

3.89 (1H, D, J = 17 Hz, C//2SO)

3^6 (1H, D, J = 17 Hz, C//2SO)

2,77 (2H, M, C//2NH2)

2,52 (1H,N,C//C02)

1.84 (1H,M,C//2CH)

1,56 (1H,M,C/i2CH)

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

1,06 (3H, D, J = 7 Hz, C/73CH).

SR 42 139 NMR-spektruma (40) 60 MHz-en: 5 (ppm)

8.45 (1H, D,J = 9 Hz, CON//)

7.30 (8H, S.e.,N//3+, C02H)

6.80 (1II, S,//tiazol)

6.00 (lH,M,//7)

5,20 (1H, AB A-ja,JAB=13Hz,C//2OCO)

4.90 (1H, AB B-je, JAB=13 Hz, CH2OCO)

4.90 (1H, D, J = 4 Hz, H6)

3.80 (3H,M,C//2SO,C//NH2)

2.00 (1H,M,C//(CH3)2)

1.45 (6H,S,(C//3)2C)

0,95 (6H, 2D, J = 7 Hz, (CH3)2CH).

SR 42 140 NMR-spektníma (41) 60 MHz-en: S (ppm)

8.50 (2H,S.e.,NH2)

8.45 (1H, D, J = 9 Hz, CON//)

7.30 (3H, S.e., N//3+)

6.80 (1H,S,// tiazol)

6.00 (lH,M,//7)

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