Ethyl Acetate → (3R)3-{4-[(5S)-5-(Acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenylamino}-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

HRID 1163329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1163329
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]([C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:34][C@H:33]([CH2:35][N:36]=[N+]=[N-])[O:32][C:31]3=[O:39])=[CH:26][C:25]=2[F:40])C(OCC2C=CC=CC=2)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:41](OCC)(=[O:43])[CH3:42]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:34][C@H:33]([CH2:35][NH:36][C:41](=[O:43])[CH3:42])[O:32][C:31]3=[O:39])=[CH:26][C:25]=2[F:40])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 8857Ethyl AcetateHCID 86597763(3R)-3-{[4-{(5R)-5-Azidomethyl-2-oxo-oxazolidin-3-yl}-2-fluoro-phenyl]-benzyloxycarbonyl-amino}-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Produkt 1

HCID 67274345(3R)3-{4-[(5S)-5-(Acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenylamino}-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

To a stirred solution of 4.2 g of (3R)-3-{[4-{(5R)-5-azidomethyl-2-oxo-oxazolidin-3-yl}-2-fluoro-phenyl]-benzyl-oxycarbonyl-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester (7.3 mmol) in 50 ml ethyl acetate were added 400 mg of Pd/C 10% and the mixture was stirred under hydrogen over night. The reaction was controlled by TLC. The Pd/C was filtered, the filtrate evaporated to dryness. The residue was dissolved in 5 ml acetic acid and 2 ml acetic anhydride was added. The reaction was stirred at rt for 2 hrs and monitored by TLC. The solvents were evaporated, the residue dissolved in ethyl acetate, washed with water and brine, dried over Mg sulfate, filtered and the filtrate evaporated to dryness.

Aufarbeitung

  1. filtrationThe Pd/C was filtered
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe residue was dissolved in 5 ml acetic acid
  4. addition2 ml acetic anhydride was added
  5. stirringThe reaction was stirred at rt for 2 hrs
  6. customThe solvents were evaporated
  7. dissolutionthe residue dissolved in ethyl acetate
  8. washwashed with water and brine
  9. dry with materialdried over Mg sulfate
  10. filtrationfiltered
  11. customthe filtrate evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-729f395242804c1189d3f88e349ac0c4
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820823B2

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