Trisodium Phosphate → Sodium (1s,5r,6s)-6-((1r)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate

HRID 1072353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072353
[OH:1][C@@H:2]([C@H:4]1[C:40](=[O:41])[N:6]2[C:7]([C:27]([O:29]CC3C=CC([N+]([O-])=O)=CC=3)=[O:28])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[O:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].P([O-])([O-])([O-])=O.[Na+:47].[Na+].[Na+].[H][H]>C1COCC1.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:40](=[O:41])[N:6]2[C:7]([C:27]([O-:29])=[O:28])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[O:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+:47]

Komponenten

6

Edukt 3

HCID 24243Trisodium PhosphateHCID 68934911(4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 131725005Sodium (1s,5r,6s)-6-((1r)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (128.5 mg) was dissolved in 6.7 ml of THF and 6.7 ml of 1/15 M sodium phosphate buffer (pH 6.6) to prepare a solution, and 130 mg of 10% Pd-C was added to the solution. The air in the reaction vessel was replaced by hydrogen, and the contents of the reaction vessel were stirred at room temperature for 2 hr. The catalyst was removed by filtration through Celite, followed by washing with water. The filtrate was washed with ethyl acetate and was then concentrated under the reduced pressure to a volume of about 2 ml. The concentrate was purified by column chromatography on Cosmosil 40C18-PREP (5% aqueous methanol solution) to give 40.9 mg of the title compound.

Aufarbeitung

  1. additionwas added to the solution
  2. customThe catalyst was removed by filtration through Celite
  3. washby washing with water
  4. washThe filtrate was washed with ethyl acetate
  5. concentrationwas then concentrated under the reduced pressure to a volume of about 2 ml
  6. customThe concentrate was purified by column chromatography on Cosmosil 40C18-PREP (5% aqueous methanol solution)

Quellen und Nachweise

ORD-Eintrag
ord-d0f5392ead5148a5a738736cbc7d0eed
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908913B2

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