[H-].[Na+].[Cl:3][C:4]1[C:5]([CH3:22])=[C:6]([S:10]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH2:19][CH2:20][OH:21])[N:18]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.C(Cl)Cl.CC(C)=O>[CH2:23]([O:21][CH2:20][CH2:19][C:17]1[N:18]=[C:14]([NH:13][S:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[C:5]=2[CH3:22])(=[O:11])=[O:12])[S:15][CH:16]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
Sodium hydride (95% dry, 76 mg, 3.00 mmol) was added to a stirred solution of EXAMPLE 181A (400 mg, 1.20 mmol) in THF (10 mL) at room temperature. After stirring for 15 min. the mixture was treated with benzyl bromide (226 mg, 1.32 mmol). After 2 h at 50° C. additional sodium hydride (60 mg, 2.40 mmol) and benzyl bromide (142 mg, 1.20 mmol) were added in two equal portions under a period of 2 h. The reaction was quenched by adding 1M HCl (3 mL) at room temperature. The mixture was extracted with DCM and dried (Sodium sulfate). Evaporation of the solvent gave a residue which was purified by flash chromatography on silica gel eluting with 5% acetone in DCM giving (105 mg, 0.25 mmol, 21%) which solidified on standing: MS (Ionspray, [M+H]+) m/z 322. Anal. Calcd. (found) for C19H19ClN2O3S2.0.5 CH2Cl2: C, 50.3 (50.7)%; H, 4.3 (4.1)%; N, 6.0 (5.9)%.
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