Br[CH2:2][C:3]([OH:5])=[O:4].[Cl:6][C:7]1[C:16]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][C:10]2[NH:11][C:12](=[S:14])[NH:13][C:9]=2[CH:8]=1.[OH-].[K+].Cl>CCO.O>[Cl:6][C:7]1[C:16]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][C:10]2[N:11]=[C:12]([S:14][CH2:2][C:3]([OH:5])=[O:4])[NH:13][C:9]=2[CH:8]=1A solution of bromoacetic acid (47.8 mg, 0.344 mmol) in EtOH (1 mL) was added dropwise to a 20 mL scintillation vial equipped with a stirring bar and a septum cap containing a solution of compound 1-3 (49.0 mg, 0.172 mmol) in EtOH (1 mL). To this solution, 1M KOH (2 mL) was added dropwise, and the resulting mixture was stirred at rt for 1 h. The reaction mixture was then diluted with water (4 mL) and acidified with 10% aqueous HCl. The solution was extracted with EtOAc (3 mL then twice 1 mL), extracts were combined and evaporated to dryness in vacuo. The resulting oily residue was dissolved in DMSO (1.0 mL), filtered and purified by reverse-phase HPLC to give the title compound as white solid. LR-MS (API-ES): calculated for C17H11ClN2O2S 342.0, observed m/e 343.1 (M+H)+ (Rt 7.71 min).
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