[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[N:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])=[C:4]([O:19][Si](C(C)(C)C)(C)C)[C:3]=1[S:27]([N:30]([CH3:32])[CH3:31])(=[O:29])=[O:28].[N:33]#[C:34]N.C([N:39](CC)C(C)C)(C)C.[F-].[Cs+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:34]#[N:33])[C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])=[NH:39])=[C:4]([OH:19])[C:3]=1[S:27]([N:30]([CH3:31])[CH3:32])(=[O:28])=[O:29]
To a solution of N-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2,3dichlorophenyl)carbodiimide (270 mg, 0.47 mmol) in acetonitrile (5 mL) at room temperature, cyanamide (79 mg, 1.88 mmol) and N,N-diisopropylethylamine (76 mg, 0.56 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was diluted with a mixture of tetrahydrofuran (3 mL) and methanol (1 mL). Cesium fluoride (86 mg, 0.56 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by Gilson HPLC to give the desired product (98 mg, 48%). EI-MS m/z 473.75(M+).
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