Cefotaxime Sodium → 1-[(1,3-Bis(n-tert-butoxycarbonyl-l-valyloxy)-2-propoxy)carbonyloxy]ethyl 3-cephem-4-carboxylate

HRID 1170686

Reaktionsgleichung

Reaktionsgleichung von HRID 1170686
[C:1](=[O:40])([O:36][CH:37](I)[CH3:38])[O:2][CH:3]([CH2:20][O:21][C:22](=[O:35])[C@H:23]([CH:32]([CH3:34])[CH3:33])[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:4][O:5][C:6](=[O:19])[C@H:7]([CH:16]([CH3:18])[CH3:17])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].CC(OC[C:46]1[CH2:67][S:66][C@@H:49]2[C@H:50](NC(/C(/C3N=C(N)SC=3)=N\OC)=O)[C:51](=[O:52])[N:48]2[C:47]=1[C:68]([O-:70])=[O:69])=O.[Na+]>CN(C=O)C>[S:66]1[C@@H:49]2[CH2:50][C:51](=[O:52])[N:48]2[C:47]([C:68]([O:70][CH:37]([O:36][C:1]([O:2][CH:3]([CH2:20][O:21][C:22](=[O:35])[C@H:23]([CH:32]([CH3:34])[CH3:33])[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:4][O:5][C:6](=[O:19])[C@H:7]([CH:16]([CH3:18])[CH3:17])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:40])[CH3:38])=[O:69])=[CH:46][CH2:67]1

Komponenten

4

Edukt 2

HCID 10695961Cefotaxime SodiumHCID 233873311,3-Bis(n-tert-butoxycarbonyl-l-valyloxy)-2-propyl 1-iodoethyl carbonate

Produkt 1

HCID 1317284161-[(1,3-Bis(n-tert-butoxycarbonyl-l-valyloxy)-2-propoxy)carbonyloxy]ethyl 3-cephem-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1,3-bis(N-tert-butoxycarbonyl-L-valyloxy)-2-propyl 1-iodoethyl carbonate (0.156 mmol) and cefotaxime sodium (67.8 mg, 0.142 mmol) in 3.2 mL dry N,N′-dimethylformamide was stirred under argon for 22 h. The reaction mixture was concentrated and subjected to column chromatography (silica, 2/1 petroleum ether-ethyl acetate, and then 20/1 CH2Cl2-methanol) to yield an oil enriched in the desired product. The oil was dissolved in 10 mL ethyl acetate, washed with water, dried, and concentrated. A second chromatography (silica, 40/1 CH2Cl2-methanol) gave the title compound (59.7 mg) as cream-colored solids.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custom20/1 CH2Cl2-methanol) to yield an oil

Quellen und Nachweise

ORD-Eintrag
ord-7477c294fec244f28c14820705292095
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825238B2

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