Pyrazole → Penicillanic Acid

HRID 485684

Reaktionsgleichung

Reaktionsgleichung von HRID 485684
[CH3:1][C:2]1([CH3:25])[S:6][C@@H:5]2[C@H:7](NC([C@H](N)C3C=CC(O)=CC=3)=O)[C:8](=[O:9])[N:4]2[C@H:3]1[C:22]([OH:24])=[O:23].CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)N2[C@H]1C([O-])=O.[K+].N1C=CC=N1.[Na]>>[CH3:1][C:2]1([CH3:25])[S:6][C@@H:5]2[CH2:7][C:8](=[O:9])[N:4]2[C@H:3]1[C:22]([OH:24])=[O:23]

Komponenten

5

Versuchsvorschrift

The free penicillanic acid of the title compound was prepared in the same manner as in Example 11(c), except that amoxycillin trihydrate was used in place of ampicillin. The free acid possessed δ(CD3OD) 1.50, 1.57(2×3H, 2s, gem dimethyls), 4.37 (1H, s, C3 penicillin proton), 5.58 (2H, m, C5 and C6 penicillin protons), 5.78 (1H, s, --CH--CONH--), 6.85(2H, d, J9 Hz, 2 aryl protons), 7.43 (2H, d, J9Hz 2 aryl protons), 7.85 (2H, d, J8Hz, 2 aryl protons), 8.30 (2H, d, J8Hz, 2 aryl protons), 8.61 (1H, s, C3 pyrazole proton). The free acid was converted to the sodium salt in a manner analogous to example 6(b). The sodium salt possessed νmax (Nujol) 1760, 1560 cm-1. MIC against E.coli NCTC 10418 5 μg/ml.

Quellen und Nachweise

ORD-Eintrag
ord-0e94331dc3184fa8b5b092eb6f6545ae
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04537886

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