Methanol → 4-Nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

HRID 1490362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1490362
O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[CH2:15]([N:17]([CH2:56][CH3:57])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][C:27]1[C@H:28]([CH3:55])[C@@H:29]2[C@@H:46]([C@H:47]([O:49][Si](C)(C)C)[CH3:48])[C:45](=[O:54])[N:30]2[C:31]=1[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33])=[O:19])[CH3:16].CO>C(Cl)Cl>[CH2:56]([N:17]([CH2:15][CH3:16])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][C:27]1[C@H:28]([CH3:55])[C@@H:29]2[C@@H:46]([C@H:47]([OH:49])[CH3:48])[C:45](=[O:54])[N:30]2[C:31]=1[C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=1)=[O:33])=[O:19])[CH3:57]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 99607884-nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate

Produkt 1

HCID 570929914-Nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-hydroxyethyl]-1-carbapen-2-em-3-carboxylateAusbeute 102,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

41 mg (0.195 mmol) of citric acid hydrate were added to 30 ml of a solution of 1.072 g (1.71 mmol) of 4-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylthio)-1-methyl-6-[1(R)-trimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 34) in a 2:1 by volume mixture of methanol and methylene chloride, and the mixture was stirred for 20 minutes at room temperature. At the end of this time, the reaction solution was condensed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 25 g of silica gel. Elution with ethyl acetate afforded 970 mg (quantitative yield) of the title compound as a colorless foam-like solid.

Aufarbeitung

  1. customcondensed
  2. distillationby distillation under reduced pressure
  3. customThe resulting residue was purified by column chromatography through 25 g of silica gel
  4. washElution with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0a0b2724d3624fdd83e2633174bc0cba
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05681951

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