Réaction #1519113

Équation de réaction

methyl bromoacetate

N-hexanoyl-4-(S)-benzyloxazolidin-2-one

NaHMDS

→

methyl 3-(R)-(n-butyl)-3-[4-(S)-benzyloxazolidin-2-one-3-ylcarbonyl)propionate

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe resulting mixture is stirred at −78° C. for 1 hour
2. 2
   Autreat rt
3. 3
   Autreovernight
4. 4
   AutreThe reaction is quenched with NH4Cl
5. 5
   Concentrationconcentrated
6. 6
   Lavagewashed with 0.5 N HCl and brine
7. 7
   Autredried
8. 8
   Autrepurified by silica gel chromatography (EtOAc/hexanes)

Mode opératoire

To a solution of N-hexanoyl-4-(S)-benzyloxazolidin-2-one A-2 (7.3 mmol) in THF at −78° C. is added 1.0 M NaHMDS (8.8 mmol) and the reaction stirred at −78° C. for 1 hour. A solution of methyl bromoacetate (8.8 mmol) in THF is then added dropwise, and the resulting mixture is stirred at −78° C. for 1 hour and then at rt overnight. The reaction is quenched with NH4Cl, concentrated, then suspended in EtOAc and washed with 0.5 N HCl and brine, dried and purified by silica gel chromatography (EtOAc/hexanes) to afford the methyl 3-(R)-(n-butyl)-3-[4-(S)-benzyloxazolidin-2-one-3-ylcarbonyl)propionate (A-3).

Source