Methanol → N-({(5S)-3-[4-(3-azabicyclo[3.1.0]hex-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl) acetamide

HRID 1814032

Reaktionsgleichung

Reaktionsgleichung von HRID 1814032
[O-]CCCC.[Li+].[CH2:7]([O:14][C:15](=[O:30])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH:27]3[CH:25]([CH2:26]3)[CH2:24]2)=[C:19]([F:29])[CH:18]=1)[C:8]1C=CC=CC=1.CO.[C:33]([NH:36][CH2:37][C@H](OC(=O)C)CCl)(=[O:35])[CH3:34].[Cl-].[NH4+]>CN(C=O)C.[Cl-].[Na+].O.O.C1COCC1>[CH:27]12[CH2:26][CH:25]1[CH2:24][N:23]([C:20]1[CH:21]=[CH:22][C:17]([N:16]3[CH2:8][C@H:7]([CH2:37][NH:36][C:33](=[O:35])[CH3:34])[O:14][C:15]3=[O:30])=[CH:18][C:19]=1[F:29])[CH2:28]2

Komponenten

10

Edukt 5

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 7357675(2S)-1-Acetamido-3-chloropropan-2-yl acetateHCID 11232635[4-(3-Aza-bicyclo[3.1.0]hex-3-yl)-3-fluoro-phenyl]-carbamic acid benzyl esterHCID 23676864Lithium butan-1-olate

Produkt 1

HCID 11290525N-({(5S)-3-[4-(3-azabicyclo[3.1.0]hex-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl) acetamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Lithium butoxide solution (2.5 mL of a 1.0 M THF solution, 2.5 mmol) was added to a cooled (0° C.) solution of [4-(3-aza-bicyclo[3.1.0]hex-3-yl)-3-fluoro-phenyl]-carbamic acid benzyl ester (0.267 g, 0.82 mmol) in DMF (0.6 mL) and MeOH (0.060 mL, 1.64 mmol). Solid (S)-acetic acid 2-acetylamino-1-chloromethyl-ethyl ester (0.316 g, 1.64 mmol) was then added and the solution allowed to warm to room temperature and stirred for 20 h. Saturated aqueous ammonium chloride (1.0 mL) was added, along with 9 mL of H2O and 8 mL of brine. The solution was extracted with three portions of dichloromethane and the combined organic phases dried (MgSO4), filtered and concentrated. The crude product was purified by column chromatography (0-3% MeOH-DCM) to provide N-({(5S)-3-[4-(3-azabicyclo[3.1.0]hex-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl) acetamide.

Aufarbeitung

  1. extractionThe solution was extracted with three portions of dichloromethane
  2. dry with materialthe combined organic phases dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (0-3% MeOH-DCM)

Quellen und Nachweise

ORD-Eintrag
ord-6bfc18fc535341e88e7b899c30916ae8
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875784B2

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