[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([NH2:18])=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CC[O:23][CH2:22]C1.Cl[C:27](OCC(C)C)=O.CONC.Cl>C(Cl)Cl>[CH3:22][O:23][N:18]([CH3:27])[C:16](=[O:17])[CH2:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1A mixture of 1.29 g (5.0 mmol) of 3-(1-(t-butoxycarbonyl)piperidin-4-yl)propionamide (from EXAMPLE 98, Step B) and 1.65 mL (15.0 mmol) of 4-methylmorpholine in 25 mL of CH2Cl2 at 0° C. was treated with 0.70 mL of isobutyl chloroformate. The resulting mixture was stirred cold for 15 min, then treated with 0.78 g (8.0 mmol) of O,N-dimethylhydroxylamine×HCl. The resulting mixture was stirred cold for 3.5 h, quenched with 100 mL of 0.5 N KHSO4, then extracted with 200 mL of ether. The extract was washed with 100 mL of 1.0 N NaOH, 50 mL of sat'd NaCM, dried and concentrated. Flash chromatography on 60 g of silica gel using 10:1 v/v, then 3:1 v/v CH2Cl2/EtOAc as the eluant afforded 1.31 g (91%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 1.07-1.18 (m, 2H), 1.38-1.69 (5H), 1.45 (s, 9H), 2.45 (t, J=7.6, 2H), 2.68 (app t, J=12.4, 2H), 3.18 (s, 3H), 3.69 (s, 3H), 4.05-4.11 (m, 2H).
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