[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:12][C@H:11]([C:13]([OH:15])=O)[C:10]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:18]1[CH:19]=[CH:20]C2N(O)N=[N:24][C:22]=2[CH:23]=1.N1CCCCC1.CCN(CC)CC>C(Cl)Cl>[CH3:16][C:10]1([CH3:17])[C@@H:11]([C:13]([N:24]2[CH2:20][CH2:19][CH2:18][CH2:23][CH2:22]2)=[O:15])[CH2:12][C@H:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]
To a stirred solution of (1S,3R)-3-(tert-butoxycarbonylamino)-2,2-dimethylcyclobutanecarboxylic acid (0.500 g, 2.057 mmol) in DCM (20 ml) EDCI (0.472 g, 2.469 mmol) and HOBt (0.378 g, 2.469 mmol) were added at 0° C. and after 10 minutes, piperidine (0.4 ml, 4.115 mmol) and Et3N (1.42 ml, 10.288 mmol) were added drop wise and the reaction mass was allowed to stir at room temperature for about 12 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with DCM and washed with water, sat. NaHCO3 solution, water, 1N HCl, water, saturated brine and the organic layer was concentrated under reduced pressure, the resulting crude residue was stirred in hexane and the resulting solid was obtained which was filtered and dried under vacuum to afford the title compound. Wt: 0.400 g; Yield: 62.79%; 1H NMR (300 MHz, CDCl3): δ 4.77 (d, 1H, J=8.4 Hz), 3.89-3.78 (m, 1H), 3.77-3.67 (m, 1H), 3.49-3.28 (m, 3H), 2.87-2.76 (m, 1H), 2.40-2.18 (m, 2H), 1.70-1.46 (m, 6H), 1.43 (s, 9H), 1.33 (s, 3H), 0.87 (s, 3H); Mass: [M+1]+ 311 (35%), [M+Na]+ 333 (100%); IR (KBr, cm−1): 3337, 2939, 1712, 1628, 1522, 1456, 1445, 1388, 1353, 1366, 1288, 1264, 1254, 1217, 1172, 1047, 1026, 1013, 976; M.R: 176.0° C.-178.0° C.
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