Sodium Bicarbonate → HCID 131714400, Verbindung

HRID 653276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 653276
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:24][O:25][C:26]([CH3:41])([C:28]([O:30]CC2C=CC([N+]([O-])=O)=CC=2)=[O:29])[CH3:27])[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15]([O:17][CH3:18])=[O:16])[N:13]([S:19]([O-:22])(=[O:21])=[O:20])[C:12]2=[O:23])=[O:9])[N:6]=1.[Na+:42].[H][H].C(=O)([O-])O.[Na+]>O.O1CCCC1.[Pd]>[Na+:42].[Na+:42].[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:24][O:25][C:26]([CH3:41])([C:28]([OH:30])=[O:29])[CH3:27])[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15]([O:17][CH3:18])=[O:16])[N:13]([S:19]([O-:22])(=[O:21])=[O:20])[C:12]2=[O:23])=[O:9])[N:6]=1.[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:24][O:25][C:26]([C:28]([OH:30])=[O:29])([CH3:27])[CH3:41])[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15]([O:17][CH3:18])=[O:16])[N:13]([S:19]([O-:22])(=[O:21])=[O:20])[C:12]2=[O:23])=[O:9])[N:6]=1

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 86740441Sodium cis-3-{2-(2-amino-4-thiazolyl)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetamido}-4-methoxycarbonyl-2-oxoazetidine-1-sulfonateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 131714400HCID 131714400, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a mixture of 25 ml of water and 25 ml of tetrahydrofuran is dissolved 500 mg of sodium cis-3-{2-(2-amino-4-thiazolyl)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetamido}-4-methoxycarbonyl-2-oxoazetidine-1-sulfonate (syn-isomer), followed by addition of 500 mg of 10% palladium-on-carbon. The mixture is stirred in a hydrogen atmosphere at room temperature for one hour. After addition of 25 ml of an aqueous solution of sodium hydrogen carbonate (62 mg), the catalyst is filtered off and the filtrate is washed with ethyl acetate and concentrated under reduced pressure. The residue is chromatographed on an Amberlite XAD-II column and lyophilized to give cis-3-[2-(2-amino-4thiazolyl)-2-(1-methyl-1-carboxyethyloxyimino)acetamido]-4-methoxycarbonyl-2-oxoazetidine-1-sulfonic acid disodium salt (syn-isomer).

Aufarbeitung

  1. filtrationthe catalyst is filtered off
  2. washthe filtrate is washed with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is chromatographed on an Amberlite XAD-II column

Quellen und Nachweise

ORD-Eintrag
ord-9c2e62cd3b5046adae42b1d6f0cc0c0a
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04675397

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