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

HRID 382651
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 382651
[C:1]([C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[C:10]([C:12]3[C@H:13]([CH3:36])[C@@H:14]4[C@@H:31]([C@H:32]([OH:34])[CH3:33])[C:30](=[O:35])[N:15]4[C:16]=3[C:17]([O:19]CC3C=CC([N+]([O-])=O)=CC=3)=[O:18])[S:9][C:8]=12)(=[O:3])[CH3:2].P([O-])([O-])([O-])=O.[Na+:42].[Na+].[Na+]>C1COCC1.[Pd]>[C:1]([C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[C:10]([C:12]3[C@H:13]([CH3:36])[C@@H:14]4[C@@H:31]([C@H:32]([OH:34])[CH3:33])[C:30](=[O:35])[N:15]4[C:16]=3[C:17]([O-:19])=[O:18])[S:9][C:8]=12)(=[O:3])[CH3:2].[Na+:42]
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Komponenten

5

Edukt 2

HCID 24243Trisodium PhosphateHCID 233882054-Nitrobenzyl (1s,5r,6s)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

Produkt 1

HCID 23698608Sodium (1s,5r,6s)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 98.2 mg of 4-nitrobenzyl (1S,5R,6S)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 5.8 ml of THF and 5.8 ml of 1/15 M sodium phosphate buffer (pH 6.6) was added 98 mg of 10% Pd-C. The reactor was purged with hydrogen, and the reaction mixture was stirred at room temperature for 2 hours. The catalyst was removed by filtration through Celite, and washed with water. The filtrate was adjusted to pH 6.5 with an aqueous sodium hydrogen carbonate solution, washed with ethyl acetate, and the aqueous layer was purified by column chromatography on DIAION HP-20 (20% methanol in water) to give 38.1 mg of the title compound.

Aufarbeitung

  1. customThe reactor was purged with hydrogen
  2. customThe catalyst was removed by filtration through Celite
  3. washwashed with water
  4. washwashed with ethyl acetate
  5. customthe aqueous layer was purified by column chromatography on DIAION HP-20 (20% methanol in water)

Quellen und Nachweise

ORD-Eintrag
ord-8f9c47fea1854c2e8acd853e0af714a9
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06310056B1

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