Sodium Chloride → HCID 118075885, compound

Temperature

0 °C

A solution of (R)—N-(2-(3-hydroxybutyl)-3-(methoxymethoxy)phenyl)acetamide (4.0 g, 14.96 mmol) in acetonitrile (40 mL) was treated with triethylamine (3.13 mL, 22.44 mmol) and cooled to 0° C. Methanesulfonyl chloride (1.46 mL, 18.7 mmol) was slowly added and a precipitate formed immediately. The slurry was stirred at 0° C. After 3 h, the reaction mixture was diluted with ethyl acetate and poured into 5% aqueous sodium chloride solution (50 mL). The layers were separated, and the organic layer washed with additional 5% aqueous sodium chloride solution (40 mL). The combined aqueous layers were extracted with ethyl acetate, and the combined organic layers were concentrated under reduced pressure. The residue was dissolved in toluene (50-75 mL), which was then removed under reduced pressure to afford (R)-4-(2-acetamido-6-(methoxymethoxy)phenyl)butan-2-yl methanesulfonate (5.17 g, 100%) as an amber syrup. The crude was used without further purification. MS (ESI, pos. ion) m/z 250 [M−95].+.

1. customa precipitate formed immediately
2. customThe layers were separated
3. washthe organic layer washed with additional 5% aqueous sodium chloride solution (40 mL)
4. extractionThe combined aqueous layers were extracted with ethyl acetate
5. concentrationthe combined organic layers were concentrated under reduced pressure
6. dissolutionThe residue was dissolved in toluene (50-75 mL)
7. customwhich was then removed under reduced pressure

ORD record

ord-f55dc42753a14b19bd2a5102fa5cdf4d

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388161B2