Methylethylenethiourea → (5R)-3-(4-(3,6-Dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-(3-methyl-2-thioxo-2,3-dihydroimidazol-1-ylmethyl)oxazolidin-2-one
Reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18]OS(C)(=O)=O)[O:15][C:14]3=[O:24])=[CH:9][C:8]=2[F:25])[CH2:3][CH2:2]1.[CH3:26][N:27]1[CH2:31][CH2:30][NH:29][C:28]1=[S:32]>>[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:29]4[CH:30]=[CH:31][N:27]([CH3:26])[C:28]4=[S:32])[O:15][C:14]3=[O:24])=[CH:9][C:8]=2[F:25])[CH2:3][CH2:2]1Participants
3
Reactant 2
Product 1
Procedure
Essentially the procedure of Example 37 was used, but starting with (5R)-3-(4-(3,6-dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-methanesulfonyloxymethyloxazolidin-2-one (300 mg, 0.81 mM), and 1-methylimidazolidin-2-thione (100 mg, 0.88 mM) and heating the reaction at 60° for 1.5 hours. Chromatography on two columns gave the desired product (29 mg).