Triethylamine → N~2~-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-D-valinamide

N-Boc-L-valine (3.72 g, 17.2 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.84 g, 18.86 mmol) were dissolved in anhydrous methylene chloride (50 mL) under nitrogen. Triethylamine (2.09 g, 20.64 mmol) was added to the mixture, followed by dropwise addition of diethyl cyanophosphonate (3.09 g, 18.92 mmol). The resulting mixture was stirred at room temperature for 12 h. The reaction was then diluted with methylene chloride (150 mL) and washed with water (100 mL). The aqueous layer was extracted with methylene chloride (50 mL). The combined organic layers were washed successively with aqueous sodium bicarbonate (2×100 mL) and brine (2×100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was carried forward without further purification. 1H NMR (CDCl3): 5.28 (d, 1H), 4.61 (m, 1H), 3.76 (s, 3H), 3.20 (s, 3H), 2.09-1.85 (m, 1H), 1.43 (s, 9H), 0.99 (d, 3H), 0.90 ppm (d, 3H).

1. washwashed with water (100 mL)
2. extractionThe aqueous layer was extracted with methylene chloride (50 mL)
3. washThe combined organic layers were washed successively with aqueous sodium bicarbonate (2×100 mL) and brine (2×100 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude residue was carried forward without further purification

ORD record

ord-095da1055b1b4e4e842ad764ab26ce5b

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07498353B2