Réaction #1519119

Équation de réaction

(S)-hydroxy-3-(2 (S)-oxazol-2-yl-pyrrolidin-1-carbonyl)-heptanoic acid methyl ester

DAST

→

2-(R/S)-fluoro-3-(2 (S)-oxazol-2-yl-pyrrolidin-1-carbonyl)-heptanoic acid methyl ester

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   LavageThe reaction mixture is washed with aqueous NaHCO3 and brine
2. 2
   Séchagedried (Na2SO4)
3. 3
   Concentrationconcentrated
4. 4
   Autrethen purified on silica gel (EtOAc/hexanes)

Mode opératoire

To 2 (S)-hydroxy-3-(2 (S)-oxazol-2-yl-pyrrolidin-1-carbonyl)-heptanoic acid methyl ester C-1 (5 mmol) in DCM (5 mL) is added DAST (15 mmol) at −20° C. The solution is stirred for 16 hours at rt. The reaction mixture is washed with aqueous NaHCO3 and brine, dried (Na2SO4) and concentrated then purified on silica gel (EtOAc/hexanes) to afford 2-(R/S)-fluoro-3-(2 (S)-oxazol-2-yl-pyrrolidin-1-carbonyl)-heptanoic acid methyl ester C-2.

Source