Water → HCID 85963598, compound

Reaction equation

[CH2:1]([C:3]1[C:4]([CH3:22])=[C:5]([C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:15])=[O:14])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[CH3:2].[Br-:23].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.O>CN(C=O)C>[Br:23][C:10]1[C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:15])=[O:14])=[C:5]([C:4]([CH3:22])=[C:3]([CH2:1][CH3:2])[CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

Procedure

To a solution of Example 130B (50 mg, 0.16 mmole) in DMF (5 mL) was added tetra-n-butylammonium tribromide (85 mg, 0.176 mmole), then water (5 mL). After stirring overnight at ambient temperature, the solvents were evaporated and the residue was partitioned between water and ethyl acetate (20 mL each). The two phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified on a silica gel column eluting with 5% methanol in dichloromethane with 1% acetic acid to provide the desired product, 70 mg (95%). 1H NMR (DMSO-d6) δ 1.2 (t, 3H), 2.04 (s, 3H), 2.55 (q, 2H), 7.15 (s, 1H), 7.25 (t, 1H), 7.68 (d, 1H0, 7.86 (t, 1H), 8.58 (d, 1H), 10.05-13.00 (br s, 2H). MS (ESI(−)) m/e 397, 399 (M−H)−.