Sodium hydride → HCID 67139799, compound

Participants

Reaction Steps

Sodium hydride (60% in mineral oil, 729 mg, 18.22 mmol) is washed twice with dry hexane and suspended in DMF (15 mL). To the suspension is added dropwise a solution of t-butoxycarbonylamino-malonic acid dimethyl ester (4.92 g, 19.9 mmol) in DMF (15 mL) over a period of 10 min. The mixture is stirred at RT for 40 min and a solution of the title D compound, 3-benzyloxy-4-nitro-benzyl iodide (6.23 g, 16.9 mmol) in DMF (15 mL) is added dropwise over a period of 10 min and the mixture is stirred at RT overnight. The mixture is diluted with water (200 mL) and extracted 3 times with EtOAc. The organic extracts are washed with water and brine, dried over anhydrous MgSO4, filtered and evaporated. The residue is crystallized from ether-hexane to give 2-(3-benzyloxy-4-nitro-benzyl)-2-t-butoxycarbonylamino-malonic acid dimethyl ester: mp=114-116° C.

Provenance & Evidence