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Phosphate → (4R,5S,6S)-3-[(2S,4S)-2-(2-aminothiazol-4-yl) pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 846958
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 846958
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C@@H:7]2[CH2:11][C@H:10]([S:12][C:13]3[C@H:19]([CH3:20])[C@H:18]4[N:15]([C:16](=[O:24])[C@@H:17]4[C@H:21]([OH:23])[CH3:22])[C:14]=3[C:25]([O:27]CC3C=CC([N+]([O-])=O)=CC=3)=[O:26])[CH2:9][N:8]2C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[N:6]=1.P([O-])([O-])([O-])=O.[H][H]>[OH-].[OH-].[Pd+2].O1CCCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C@@H:7]2[CH2:11][C@H:10]([S:12][C:13]3[C@H:19]([CH3:20])[C@H:18]4[N:15]([C:16](=[O:24])[C@@H:17]4[C@H:21]([OH:23])[CH3:22])[C:14]=3[C:25]([OH:27])=[O:26])[CH2:9][NH:8]2)[N:6]=1
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Komponenten

6

Edukt 3

HCID 1061PhosphateHCID 57238971HCID 57238971, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 57177244(4R,5S,6S)-3-[(2S,4S)-2-(2-aminothiazol-4-yl) pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidAusbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167
Palladium hydroxide
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(2-aminothiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (900 mg), 20% palladium hydroxide on carbon (350 mg), 0.05M phosphate buffer (pH 6.5, 20 ml) and tetrahydrofuran (30 ml) was stirred at room temperature for 3 hours under atmospheric pressure of hydrogen. After the catalyst was filtered off, the filtrate was concentrated to remove the organic solvent. The residue was washed with ethyl acetate, adjusted to pH 6.2 with aqueous potassium carbonate and concentrated in vacuo to remove the organic solvent. The residue was chromatographed on nonionic adsorption resin "Diaion HP-20" (Trademark, made by Mitsubishi Chemical Industries) (60 ml) eluting in turn with water (250 ml) and 5-7% aqueous acetone (200 ml). The fractions containing the desired compound were collected and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-2-(2-aminothiazol-4-yl) pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (233 mg).

Aufarbeitung

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customto remove the organic solvent
  4. washThe residue was washed with ethyl acetate
  5. concentrationconcentrated in vacuo
  6. customto remove the organic solvent
  7. customThe residue was chromatographed on nonionic adsorption resin "Diaion
  8. wash" (Trademark, made by Mitsubishi Chemical Industries) (60 ml) eluting in turn with water (250 ml) and 5-7% aqueous acetone (200 ml)
  9. additionThe fractions containing the desired compound
  10. customwere collected

Quellen und Nachweise

ORD-Eintrag
ord-6d7f31ef82c54fb4b013b4696811ab63
Quelldatensatz
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05138064

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