C(O)(=O)C.CCN(CC)CC.[C:12]([C@@H:14]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)#[N:13].[N-:30]=[N+:31]=[N-:32].[Na+]>C1(C)C=CC=CC=1>[C:16]1([CH2:15][C@H:14]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[C:12]2[NH:32][N:31]=[N:30][N:13]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1To a solution of acetic acid (93 μL, 1.62 mmol) in PhMe (2.0 mL) was added Et3N (226 μL, 1.624 mmol). (S)-tert-Butyl (1-cyano-2-phenylethyl)carbamate (100 mg, 0.41 mmol) was then added to the mixture followed by NaN3 (106 mg, 1.62 mmol). The resulting reaction mixture was heated at 100° C. for 2 h and then filtered, rinsing with EtOAc. The filtrate was concentrated in vacuo and purified using preparative HPLC to give the title compound (100 mg, 85%) as a white solid after lyophilization. 1H NMR (CDCl3) δ 7.37-7.20 (m, 3H), 7.12 (d, J=6.6 Hz, 2H), 5.56 (br s, 1H), 5.30 (d, J=6.2 Hz, 1H), 3.35 (d, J=6.4 Hz, 2H), 1.51-1.17 (m, 9H); MS (ESI+) m/z 290.2 (M+H)+.
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