[Cl:1][S:2]([N:5]=C=O)(=[O:4])=[O:3].[S:8](Cl)(=[O:11])(=[O:10])[NH2:9].[CH2:13]([O:15][C:16](=[O:29])[CH2:17][NH:18][CH2:19][C:20]1[O:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[CH:24]=1)[CH3:14].Cl>C(Cl)Cl.C(N(CC)CC)C.C(O)=O>[S:2]([Cl:1])(=[O:4])(=[O:3])[NH2:5].[CH2:13]([O:15][C:16](=[O:29])[CH2:17][N:18]([CH2:19][C:20]1[O:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[CH:24]=1)[S:8](=[O:11])(=[O:10])[NH2:9])[CH3:14]
A stock of sulfamyl chloride was prepared by adding formic acid to chlorosulfonyl isocyanate. The sulfamyl chloride was added to a room temperature solution of 104 and triethyl amine in methylene chloride. The reaction was stirred at room temperature overnight. TLC (30% ethyl acetate/hexanes) showed a major spot and a minor product. The reaction was poured into 10% HCl, extracted with methylene chloride, dried over sodium sulfate, filtered, and concentrated to a thick yellow syrup. The crude syrup was adsorbed onto silica and purified by flash chromatography with 15-30% ethyl acetate/hexanes to obtain the final product 105 as a light yellow film.
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