Sodium hydride → 12-(tert-Butoxycarbonyl)-6,12-bis(benzyloxy)-7-oxo-6,12-diazadodecanenitrile

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N-(tert-Butoxycarbonyl)-O-benzylhydroxylamine (4.2 g, 18.8 mmol) was dissolved in DMF (120 mL) and cooled to 0° C. Sodium hydride (80%, 0.564 g, 18.8 mmol) was added, and the mixture was stirred at 0° C. for 30 minutes. A solution of (3) (6.0 g, 18.6 mmol) in DMF (30 mL) was slowly added to the cold solution which was then allowed to stir at room temperature for 20 minutes and at 80° C. overnight. The DMF was removed under high vacuum, and the reside was quenched with H2O (50 mL) and extracted with CH2Cl2 (3×70 mL). Organic extracts were washed with saturated sodium chloride, and the solvent was removed by rotary evaporation. Silica gel column chromatography, eluting with 2:1 hexane/EtOAc produced 7.29 g (77%) of (4) as an oil: NMR δ 1.50 (s, 9H), 1.40-1.90 (m, 8H), 2.30 (t, 2H, J=6), 2.40 (t, 2H, J=6), 3.40 (t, 2H, J=6), 3.63 (t, 2H, J=6), 4.77 (s, 2H), 4.80 (s, 2H), 7.33 (s, 10H) . Anal. (C29H39N3O5), C, H, N.

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