O1CCOCC1.Cl.[NH2:8][C:9]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:10]=1[C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]1)=[O:16])=[O:12]>CO>[NH2:8][C:9]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:10]=1[C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][CH:19]1[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]1)=[O:16])=[O:12]A 4 M dioxane solution of HCl (9.5 mL) was added to a methanol (20 mL) solution of 4-[[(N-(2-amino-5-chlorobenzoyl)glycyl)amino]methyl]-1-(tert-butoxycarbonyl)piperidine (1.63 g, 3.84 mmol), and the resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated, and a 2 M aqueous solution of NaOH (20 mL) was added to the resulting residue. The obtained mixture was extracted with dichloromethane (20 mLX 3). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated to thereby afford 4-[[(N-(2-amino-5-chlorobenzoyl)glycyl)amino]methyl]piperidine (1.19 g, 95%). 1H NMR (CDCl3, 270 MHz) δ 1.10-1.76 (m, 4H), 2.55 (td, J=2.4 and 12.2 Hz, 2H), 3.00-3.10 (m, 2H), 3.17 (t, J=6.2 Hz, 2H), 3.48 (s, 2H), 4.03 (d, J=4.9 Hz, 2H), 5.50 (br. s, 2H), 6.11-6.23 (m, 1H), 6.60 (d. J=8.8 Hz, 1H), 6.85-7.02 (m, 1H), 7.15 (dd, J=2.7 and 8.8 Hz, 1H), 7.38 (d, J=2.4 Hz, 1H). ESI/MS m/e 325.2 (M++H, C15H23ClN4O2).
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