Reaktion #5497

ord-ee7debe1bbd340b6a45aa36abc48f31c

Reaktionsgleichung

CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O
Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid
BrCc1ccccc1
Benzyl bromide
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
→
CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)OCc2ccccc2)NC1=O
trans benzyl 3-(acetylthiomethyl)-2-oxo-1-aza-cyclodecane-10-carboxylate

Edukte

CC(=O)SC[C@H]1CCCCCC[C@H](C(=O)O)NC1=O
Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid
BrCc1ccccc1
Benzyl bromide
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionthe aqueous layer is extracted several times with methylene chloride
  2. 2
    TrocknenThe combined organic layers are dried (MgSO4)
  3. 3
    Sonstigethe solvent is evaporated
  4. 4
    SonstigeThe product is purified by silica gel chromatography (10% ethyl acetate/hexane)

Vorschrift

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.15 g, 0.52 mmol) is dissolved in dimethylformamide (2.5 mL). Benzyl bromide (0.062 mL, 0.52 mmol) and cesium carbonate (0.085 g, 0.26 mmol) are added, and the reaction is stirred at room temperature overnight. The reaction is diluted with water, and the aqueous layer is extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (10% ethyl acetate/hexane) to give trans benzyl 3-(acetylthiomethyl)-2-oxo-1-aza-cyclodecane-10-carboxylate m.p. 117°-118° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05244889uspto-grants-1993_09