Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 54159751, compound

Temperature

5 °C

N-tert-Butoxycarbonyl-L-leucine monohydrate (2.5 g, 10 mmol, Bachem Inc., Torrance, Calif.) was dissolved in dry DMF (15 mL) under nitrogen atmosphere and cooled to 5° C. To this solution were added, in succession, N,N-diisopropylethylamine (5.3 mL, 30 mmol) and solid O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.8 g, 10 mmol). The resulting reaction mixture was stirred at that temperature for 30 minutes; O,N-dimethylhydroxylamine hydrochloride (1.1 g, 11 mmol, Aldrich, Milwaukee, Wis.) was then added. After additional 30 minutes stirring at 0° C., the reaction mixture was mixed with 75 mL of diethyl ether; the resulting mixture was successively washed with 5% aqueous HCl solution (50 mL), brine (50 mL), saturated aqueous NaHCO3 solution (50 mL), brine (2×50 mL), and was dried over Na2SO4. The solution was concentrated in vacuo affording 2.3 g of desired product as a clear oil which was used in the subsequent reaction without further purification.

1. customThe resulting reaction mixture
2. stirringAfter additional 30 minutes stirring at 0° C.
3. washthe resulting mixture was successively washed with 5% aqueous HCl solution (50 mL), brine (50 mL), saturated aqueous NaHCO3 solution (50 mL), brine (2×50 mL)
4. dry with materialwas dried over Na2SO4
5. concentrationThe solution was concentrated in vacuo

ORD record

ord-ff2c48caebc34db19457c04e99ee3d7c

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458781B1