[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][C:5]1(C(O)=O)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.C1(P([N:39]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CC#N>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([NH2:39])([CH2:4][C:3]2[CH:21]=[CH:22][CH:23]=[CH:24][C:2]=2[CH3:1])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]To a mixture of 4-(2-methylbenzyl) N-t-butoxycarbonyl isonipecotic acid (1.0 g, 3.0 mmol) in CH3CN (20 ml) add diphenyl phosphoryl azide (0.99 g, 3.6 mmol) and triethylamine (0.50 ml, 3.6 mmol). After stirring at 55° C. (oil bath temp.) concentrate the reaction in vacuo and partion the residue between EtOAc and saturated aqueous NaHCO3. The organic phase is washed with brine, dried (MgSO4), and concentrated in vacuo to afford the crude product.
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