Reaktion #1894330

Reaktionsgleichung

DIPEA

3-aminophenyl-methanesulfonamide

rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid

HATU

→

rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (3-methanesulfonylamino-phenyl)-amide

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with addition of water
2. 2
   ExtraktionThe mixture was extracted with methylene chloride (2×10 mL)
3. 3
   Trocknenthe extracts were dried with magnesium sulfate
4. 4
   SonstigeThe solvent was removed
5. 5
   Sonstigethe residue was purified on an ISCO machine (40 g column, eluent, 35-80% EtOAc/hexanes)
6. 6
   Sonstigeto give a white solid

Vorschrift

To a stirred solution of rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (100 mg, 0.22 mmol) in methylene chloride (10 mL), HATU (Aldrich, 83 mg, 0.22 mmol) was added followed by the addition of DIPEA (0.20 mL) and 3-aminophenyl-methanesulfonamide (Aldrich, 0.25 mmol). The mixture was stirred at rt 1 hr. The reaction was quenched with addition of water. The mixture was extracted with methylene chloride (2×10 mL) and the extracts were dried with magnesium sulfate. The solvent was removed and the residue was purified on an ISCO machine (40 g column, eluent, 35-80% EtOAc/hexanes) to give a white solid. 64 mg.

Quelle