[OH:1][C@@H:2]([CH:6]([CH3:8])[CH3:7])[C:3](O)=[O:4].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH2:23][CH2:24][C:25]1([C:30]([O:32][CH3:33])=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.O>[OH:1][C@@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([NH:23][CH2:24][C:25]1([C:30]([O:32][CH3:33])=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:4]To a solution of (S)-2-hydroxy-3-methyl-butyric acid (300 mg, 2.5 mmol) in CH2Cl2/DMF (5:1, 20 mL) at 0° C. was added HOBT (382 mg, 2.5 mmol) and EDC (477 mg, 2.5 mmol). The mixture was stirred for 10 min then methyl 1-(aminomethyl)cyclopentanecarboxylate (321 mg, 2.25 mmol) and iPr2NEt (0.5 mL, 2.5 mmol) were added and stirring was continued for 3 h. The reaction was diluted with water and extracted with EtOAc. The combined extracts were washed with water, 1N HCl, sat'd NaHCO3, dried over magnesium sulfate, concentrated, and purified using flash chromatography to give a white solid (420 mg, 72%). MS [M+H]+258.
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