Water → (2S)-2,3-Dihydroxy-N-methoxy-2,N-dimethyl-propionamide

A round bottom flask was charged with 3BuOH (850 mL), water (850 mL), Ad-Mix-β (230 g, 166 mmol) and methanesulfonamide (15.8 g, 166 mmol). The mixture was stirred at ambient temperature until both phases were clear (about 5 minutes) and then cooled to 0° C., after which orange salts precipitated. N-methoxy-N-methylmethacrylamide (21.5 g, 166 mmol) was added and the heterogeneous slurry was stirred vigorously 0° C. for 2 hours and warmed to ambient temperature and stirred for 24 hours. The reaction was quenched by the slow, portionwise addition of sodium bisufite (223 g) and stirred for 1 hour. The reaction mixture was extracted with EtOAc (3×300 mL), dried over sodium sulfate, filtered and concentrated to afford (S)-2,3-dihydroxy-N-methoxy-N,2-dimethylpropanamide (32 g, 196 mmol, 118% yield) as a yellow oil.

1. custom(about 5 minutes)
2. temperaturecooled to 0° C.
3. customafter which orange salts precipitated
4. stirringthe heterogeneous slurry was stirred vigorously 0° C. for 2 hours
5. temperaturewarmed to ambient temperature
6. stirringstirred for 24 hours
7. customThe reaction was quenched by the slow,
8. additionportionwise addition of sodium bisufite (223 g)
9. stirringstirred for 1 hour
10. extractionThe reaction mixture was extracted with EtOAc (3×300 mL)
11. dry with materialdried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-4a3ebd43626b4d9aae1cb6d7fa0fe340

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853409B2