4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate → FR-27743

HRID 703598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 703598
[F:1][CH2:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:10][C@H:9]([S:11][C:12]2[C@H:18]([CH3:19])[C@H:17]3[N:14]([C:15](=[O:23])[C@@H:16]3[C@H:20]([OH:22])[CH3:21])[C:13]=2[C:24]([O:26]CC2C=CC([N+]([O-])=O)=CC=2)=[O:25])[CH2:8][N:7]1C(OCC1C=CC([N+]([O-])=O)=CC=1)=O.[H][H]>O1CCCC1.P([O-])([O-])([O-])=O.[OH-].[OH-].[Pd+2]>[F:1][CH2:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:10][C@H:9]([S:11][C:12]2[C@H:18]([CH3:19])[C@H:17]3[N:14]([C:15](=[O:23])[C@@H:16]3[C@H:20]([OH:22])[CH3:21])[C:13]=2[C:24]([OH:26])=[O:25])[CH2:8][NH:7]1

Komponenten

6

Edukt 2

HCID 571170454-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86744488FR-27743Ausbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 1061PhosphateLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.80 g) in a mixture of tetrahydrofuran (50 ml) and 0.1M phosphate buffer (pH 5.8) (50 ml) was stirred at ambient temperature for 5 hours in the presence of 20% palladium hydroxide on carbon (0.3 g) under atmospheric pressure of hydrogen. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to remove tetrahydrofuran. The resulting aqueous solution was washed with ethyl acetate (50 ml×2) and evaporated to remove the organic solvent. The residual solution was subjected to a column chromatography on nonionic adsorption resin, "Diaion HP-20" (trademark, made by Mitsubishi Chemical Industries) (50 ml) and eluted with a mixture of acetone and water (5:95 V/V). The fractions containing the desired compound were combined and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.20 g).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto remove tetrahydrofuran
  4. washThe resulting aqueous solution was washed with ethyl acetate (50 ml×2)
  5. customevaporated
  6. customto remove the organic solvent
  7. wash" (trademark, made by Mitsubishi Chemical Industries) (50 ml) and eluted with a mixture of acetone and water (5:95 V/V)
  8. additionThe fractions containing the desired compound

Quellen und Nachweise

ORD-Eintrag
ord-af48521cb6cd4809a50ff9fa99578da0
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04983596

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