Cl.Cl.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:12][CH2:13][CH2:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH2:17])[CH3:11])=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.Cl[C:34](Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.CCOCC>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]([N:12]2[CH2:13][CH2:14][CH2:15][CH:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:17][C:34]2=[O:36])[CH3:11])=[CH:8][CH:9]=1
A stirred solution of N1—((1S)-1-(4-bromophenyl)ethyl)-4-phenylbutane-1,4-diamine dihydrochloride (19.5 mg, 0.046 mmol) and i-Pr2NEt (0.10 mL, 0.56 mmol) in CH2Cl2 (8 mL) was cooled in an ice bath and solid triphosgene (4.6 mg, 0.015 mmol) was added. The ice bath was allowed to melt and the mixture was stirred overnight at rt. The mixture was diluted with ether (90 mL), washed with 5% aq HCl (20 mL) and satd aq NaHCO3 (20 mL), and dried over MgSO4. Removal of the solvent left a residue (17.5 mg) which was purified by preparative HPLC to afford 1-((S)-1-(4-bromophenyl)ethyl)-4-phenyl-1,3-diazepan-2-one (1.4 mg, 8%). LC-MS (3 min) tR=2.05 min, m/z=375, 373.
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