(4R)-4-phenyl-1,3-oxazolidin-2-one → 3-[(2-fluorophenyl)-acetyl]-4(R)-phenyl-2-oxazolidinone

HRID 1638156

Reaktionsgleichung

Reaktionsgleichung von HRID 1638156
[C:1]1([C@@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26](Cl)=[O:27]>C1COCC1>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([N:8]1[C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][O:10][C:9]1=[O:12])=[O:27]

Komponenten

5

Edukt 3

HCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-oneHCID 140040112-(2-Fluorophenyl)acetyl chlorideHCID 178418339Butyllithium

Produkt 1

HCID 111506973-[(2-fluorophenyl)-acetyl]-4(R)-phenyl-2-oxazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a -78° C. solution of 4(R)-phenyl-2-oxazolidinone (340 g, 2.08 mol) in THF (8000 mL), is added n-BuLi (2.5 M, 920 mL, 1.1 eq). The reaction mixture is stirred for 20 minutes and 2-fluorobenzeneacetyl chloride (358 g, 2.08 mol) is added. After 2 hours the reaction mixture is quenched with saturated NH4Cl solution (1×1000 mL). The organic layer is separated, washed with H2O (1×1000 mL), saturated NaCl solution (2×1000 mL) and then concentrated in vacuo. This procedure yields 3-[(2-fluorophenyl)-acetyl]-4(R)-phenyl-2-oxazolidinone.

Aufarbeitung

  1. customAfter 2 hours the reaction mixture is quenched with saturated NH4Cl solution (1×1000 mL)
  2. customThe organic layer is separated
  3. washwashed with H2O (1×1000 mL), saturated NaCl solution (2×1000 mL)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bac363c1e0034e2d8bd66aedf913326f
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06043365

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