[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][C:7]1[C:8]([F:30])=[C:9]([F:29])[C:10]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:11]([CH:19]=1)[C:12]([NH:14][O:15][CH2:16][CH2:17][OH:18])=[O:13].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:33](=[O:34])C1.C(N(CC)CC)C>C1COCC1.CC#N>[F:29][C:9]1[C:10]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:11]([CH:19]=[C:7]([CH2:6][N:5]2[CH2:4][CH2:3][CH2:2][NH:1][C:33]2=[O:34])[C:8]=1[F:30])[C:12]([NH:14][O:15][CH2:16][CH2:17][OH:18])=[O:13]The amine synthesized in Step A (66.4 mg, 0.1233 mmol) was dissolved in THF:CH3CN (1:1 v/v, 3.0 ml). N,N-disuccinimidyl carbonate (47.4 mg, 1.5 eq., 0.1849 mmol) and triethylamine (103.1 μl, 6.0 eq., 0.7398 mmol) were added sequentially to this solution, and the mixture was stirred at room temperature for 20 hours. The solvent was removed under reduced pressure, and the residue was purified by LC/MS to give white crystals (42.6 mg).
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