1,2-Dichloroethane → HCID 86594383, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of O-tert-butyl hydroxylamine hydrochloride (3.67 g, 29.3 mmol) in dry THF (30 mL) at room temperature was added diisopropylethyl amine (3.60 g, 27.9 mmol). To the resulting mixture was transferred the compound of example 58 (6.87 g, 27.9 mmol), as a solution in dry THF (30 mL), followed by HOBt (5.35 g, 27.9 mmol). The mixture was cooled to 0° C. and EDC (5.35 g, 27.9 mmol) was added in one portion. The reaction mixture was then allowed to warm to room temperature and was stirred for 24 h. The solvent was evaporated and the residue was taken-up into 500 ml of ethyl acetate and subsequently washed with a 5% aqueous solution of KHSO4 (2×200 mL), with a 5% aqueous solution of NaHCO3 (2×200 mL), and finally with water. After drying (anhydrous MgSO4) and evaporation, the crude product was purified by flash chromatography (SiO2, 60% hexane-40% ethyl acetate) to afford 5.93 g (66.0% yield) of the desired product: 1H NMR (CDCl3, 400 MHz) 8.61 (s, 1H), 4.20 (q, 2H), 3.55 (t, 1H), 2.93 (d, 3H), 1.43 (s, 9H), 1.28 (s, 9H); 13C NMR (CDCl3, 400 MHz) 195.8, 171.2, 169.7, 83.1, 81.9, 62.4, 46.8, 34.1, 28.4, 26.6, 14.5.

Provenance & Evidence