Sodium Hydroxide → HCID 15117344, compound

A solution of (2R,3R)-1,2-bis(benzyloxycarbonylamino)-3-hydroxybutane (80.5 g) in methanol (800 ml) was hydrogenated under atmospheric pressure of hydrogen over palladium on carbon (10%, 8 g) for 5 hours at ambient temperature. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give a syrup. To a solution of the syrup in a mixture of water (400 ml) and tetrahydrofuran (400 ml) in tetrahydrofuran (90 ml) under ice-cooling with stirring, keeping the pH between 8.5 and 9.5 with 4N aqueous sodium hydroxide. After stirring for one hour, the mixture was extracted with ethyl acetate (800 ml), washed with brine (400 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (600 g) and eluted with a mixture of methanol and chloroform (1:99, V/V) to give (2R,3R)-1,2-bis(allyloxycarbonylamino)-3-hydroxybutane (41.78 g) as a syrup.

1. filtrationThe catalyst was filtered off
2. concentrationthe filtrate was concentrated under reduced pressure
3. customto give a syrup
4. temperaturecooling
5. stirringAfter stirring for one hour
6. extractionthe mixture was extracted with ethyl acetate (800 ml)
7. washwashed with brine (400 ml)
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customto give a syrup
11. washeluted with a mixture of methanol and chloroform (1:99, V/V)

ORD record

ord-57e31377f4854351ab7f0e274a4153a0

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05102877