Ethyl Acetate → tert-butyl N-(2-anilinophenyl)glycinate

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Reaction Steps

To a stirring solution of N-phenyl-o-phenylene diamine (20 g, 180.55 n M) in 200 ml of DMF at RT was added K2CO3 (16.5 g, 120 mM) followed by tert-butyl bromoacetate (21.17 g 108.55 mM). The resulting mixture was stirred at RT until TLC (Hex:AcOEt 3:1) showed completion of reaction. The mixture was filtered to remove the K2CO3 and then diluted with 800 mL of EtOAc and 200 mL of Et2O. This solution was washed successively with H2O (2×400 mL), brine (1×400 mL), 1 N HCl (2×400 mL), and H2O (1×400 mL), and the organics dried (MgSO4) and concentrated to give a greenish-black oil. The resultant oil was purified by silica gel flash column chromatography using hexane/EtOAc 4/1 and the combined filtrates evaporated in vacuo to give 30 g of product.

Provenance & Evidence