Methane → Sodium 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 371283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 371283
[F:1][C:2]([F:30])([F:29])[CH:3]([CH:5]1[C:11](=[O:12])[N:10]2[CH:6]1[CH2:7][C:8]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[C:9]2[C:13]([O:15]CC1C=CC=CC=1)=[O:14])[OH:4].C.C(=O)(O)[O-].[Na+:36].O1CCOCC1>[Pd].O>[F:30][C:2]([F:1])([F:29])[CH:3]([CH:5]1[C:11](=[O:12])[N:10]2[CH:6]1[CH2:7][C:8]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[C:9]2[C:13]([O-:15])=[O:14])[OH:4].[Na+:36]

Komponenten

7

Edukt 4

HCID 297MethaneHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 20160992Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Produkt 1

HCID 23674972Sodium 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (25 mg), 10% palladium on powdered charcoal (25 mg), sodium bicarbonate (5 mg), dioxane (2 ml), and water (1 ml) is hydrogenated at 40 psi for 30 mins. The mixture is filtered to remove the catalyst which is washed with water (3×3 ml). The combined filtrate is extracted with ethyl acetate (2×2 ml), concentrated in vacuo, and lyophilized to give sodium 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-morpholino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Aufarbeitung

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst which
  3. washis washed with water (3×3 ml)
  4. extractionThe combined filtrate is extracted with ethyl acetate (2×2 ml)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e1ee7f61a5a74fafaa458c65984b1987
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04530841

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