[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN([C:25]([O:29][N:30]1N=NC2C=CC=C[C:31]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.CNOC>CN(C)C=O>[CH3:25][O:29][N:30]([CH3:31])[C:17]([C:16]1[CH:20]=[CH:21][C:13]([C:9]2([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:12][CH2:11][CH2:10]2)=[CH:14][CH:15]=1)=[O:19]To a solution of 4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)benzoic acid (2.5 g, 1 eq.) in dimethylformamide (10 mL) was added HBTU (3.41 g, 1.05 eq.) followed by triethylamine (6 mL, 5 eq.). The reaction mixture was stirred at room temperature for 10 minutes then the N,O-dimethylhydroxylamine hydrochloride was added (4.3 g, 5 eq.) and the mixture was stirred for 3 days. The reaction mixture was poured onto water (50 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water (100 mL), brine (100 mL) then dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (20-50% ethyl acetate in dichloromethane), giving tert-butyl (1-(4-(methoxy(methyl)carbamoyl)phenyl)cyclobutyl)carbamate (1.5 g, 52%). LCMS: 335 [M+H].
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