Water → HCID 58392224, compound

Reaction equation

Br[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:9]=[CH:8]2.[CH3:19][S-:20].[Na+].O>CN(C)C=O>[C:15]([O:14][C:12]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:2][S:20][CH3:19])[CH:8]=[CH:9]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

Procedure

160 mg (516 μmmol) of the compound from Example 6A and 36.2 mg (516 μmol) of sodium methanethiolate were stirred in 5 ml of dimethylformamide at RT for three days. Water was then added, and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate gradient) to result in 64 mg (45% of theory) of the title compound.