Lawesson's reagent → (S)-benzyl 2-(2-bromophenylcarbamothioyl)-2-methylpyrrolidine-1-carboxylate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@:11]1([CH3:26])[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@:11]1([CH3:26])[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[S:36]Participants
4
Procedure
To a solution of EXAMPLE 5B (1.25 g) in toluene (12 mL) was added Lawesson's reagent (1.212 g) and the mixture heated at reflux for 5 hours. After cooling, the solid was filtered and the filtrate concentrated. The residue was dissolved in ethyl acetate and the solution washed with 5% aqueous citric acid and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated, and the residue purified by flash chromatography on silica gel using 4:6 to 6:4 dichloromethane/hexane to afford the title compound.