1,2-Dichloroethane → Tert-butyl {3-[methoxy(methyl)amino]-2-methyl-3-oxopropyl}carbamate

3-[(tert-Butoxycarbonyl)amino]-2-methylpropanoic acid (2.0 g, 9.9 mmol) was dissolved in acetonitrile (50 mL). To this solution was added HOBT (1.6 g, 11.85 mmol) and EDC (2.0 g, 10.4 mmol). The reaction was stirred at room temperature for 2 hr, and then treated with triethylamine (2.8 mL, 20 mmol) and N,O-dimethylhydroxyamine hydrochloride (2.0 g, 20 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was quenched with water and extracted with ethyl acetate (3×). The combined organic extract was washed sequentially with 0.5N hydrochloric acid, 1N aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on a Biotage® system (silica, 40-100% ethyl acetate in hexanes) to yield tert-butyl {3-[methoxy(methyl)amino]-2-methyl-3-oxopropyl}carbamate as white solid. MS (M+1−Boc): 147.

1. stirringThe reaction mixture was stirred at room temperature overnight
2. customThe reaction was quenched with water
3. extractionextracted with ethyl acetate (3×)
4. extractionThe combined organic extract
5. washwas washed sequentially with 0.5N hydrochloric acid, 1N aqueous sodium bicarbonate solution and brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe crude product was purified by flash chromatography on a Biotage® system (silica, 40-100% ethyl acetate in hexanes)

ORD record

ord-89286bb8b89e49aeb96b844fc08de52d

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259160B2