Reaktionsgleichung
C[Si](C)(C)OC([NH:6][C@@H]1C(=O)N2C(C(O[Si](C)(C)C)=O)=C(COC(=O)C)CS[C@H]12)=O.[Si](I)(C)(C)C.C([O-])(=O)C.C[Si](C)(C)OC(N[C@@H:45]1[C:61](=[O:62])[N:47]2[C:48]([C:54]([O:56][Si:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])=[C:49]([CH2:52][I:53])[CH2:50][S:51][C@H:46]12)=O.C[C:66]([O:68][Si:69]([CH3:72])([CH3:71])[CH3:70])=[O:67]>ClCCl>[CH3:70][Si:69]([CH3:72])([CH3:71])[O:68][C:66]([C@H:45]1[C:61](=[O:62])[N:47]2[C:48]([C:54]([O:56][Si:57]([CH3:58])([CH3:59])[CH3:60])=[O:55])=[C:49]([CH2:52][I:53])[CH:50]([NH2:6])[S:51][C@H:46]12)=[O:67]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred solution of (6R, 7R)-trimethylsilyl 7-[((trimethylsilyl)oxy)carbonyl]amino-3-acetoxymethylceph-3-em-4-carboxylate in dichloromethane (prepared according to Method B of Example 2; 5.0 g input 7-ACA) was added 3.0 ml (21.1 mmoles, 1.15 equivalents) of TMSI in a slow stream at ambient temperature under a blanket of dry nitrogen. The progress of the reaction was monitored by 1H NMR (acetate region). After a total of 65 minutes, the 1H NMR spectrum of an aliquot of the dark solution shows >95% conversion to the desired (6R, 7R)-trimethylsilyl 7-[((trimethylsilyl)oxy)carbonyl]amino-3-iodomethylceph-3-em-4-carboxylate: NMR (CD2Cl2) δ0.27 (br s, 9H --NHCOOSi(CH3)3), overlapped with CH3COOSi(CH3)3), 0.37 (s, 9H, --COOSi(CH3)3), 3.57 (d, 1H, J=18.1 Hz, --SCH2), 3.80 (d, 1H, J=18.1 Hz, --SCH2), 4.34 (d, 1H, J=9.2 Hz, --CH2I), 4.51 (d, 1H, J=9.2 Hz, --CH2I), 5.00 (d, 1H, J=4.6 Hz, --COCH(N)CH(N)SCH2 --); the remainder of the spectrum was obliterated by protonic dichloromethane.
Aufarbeitung
- customAfter a total of 65 minutes
Quellen und Nachweise
- ORD-Eintrag
- ord-e4df2a4a5ac34abaa07ce1dbf47ee817
- Quelldatensatz
- uspto-grants-1989_09
- Patentnummer
- US04868294
Verknüpfte Notizen
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