[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].C1C=CC2N(O)N=NC=2C=1.[CH2:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH3:29].CCN(CC)CC>C(Cl)Cl>[CH2:28]([N:30]1[CH2:35][CH2:34][N:33]([C:13]([C@H:11]2[CH2:12][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]2([CH3:17])[CH3:16])=[O:15])[CH2:32][CH2:31]1)[CH3:29]To a stirred solution of (1S,3R)-3-(tert-butoxycarbonylamino)-2,2-dimethylcyclobutanecarboxylic acid (2 g, 8.23 mmol) in DCM (50 ml) EDCI (946 mg, 9.876 mmol) and HOBt (756 mg, 9.876 mmol) were added at 0° C., after 10 minutes N-Ethyl piperazine (939 mg, 16.46 mmol) and Et3N (3 mL, 41.15 mmol) were added drop wise and the reaction mass was allowed to stir at room temperature for 12 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with DCM and washed with water, saturated NaHCO3 solution, water, 1N HCl, water and saturated brine and the organic layer was concentrated under reduced pressure. The resulting crude residue was stirred in hexane and obtained solid was filtered. Wt: 1.6 g; Yield: 70%. 1H NMR (300 MHz, CDCl3): δ 4.77 (d, 1H, J=8.4 Hz), 3.89-3.78 (m, 1H), 3.6-3.46 (m, 3H), 2.80 (m, 1H), 2.60-2.40 (m, 8H), 1.80 (m, 1H), 1.43 (s, 9H), 1.12 (s, 3H), 1.2 (t, 3H), 0.87 (s, 3H); Mass: [M+1]+ 340 (25%), [M+Na]+ 362 (100%).
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