Sodium hydride → HCID 59976013, compound

Temperature

0 °C

A solution of N—BOC-D-serine (2.00 g, 9.75 mmol) in DMF (25 ml) was cooled to 0° C. under nitrogen atmosphere and sodium hydride (60% in mineral oil) (0.82 g, 20.47 mmol) was added portionwise over 15 minutes. After stirring at 0° C. for 30 minutes, 4-fluorobenzyl bromide (1.82 g, 9.75 mmol) in DMF (5 ml) was added. The ice bath was removed and the reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between EtOAc (100 ml) and water (50 ml). The aqueous phase was separated and washed with DCM (2×50 ml). The organic washings were discarded. The aqueous layer was acidified with 5% citric acid aqueous solution and back-extracted with DCM (2×100 ml). The combined organic portions were washed with brine (50 ml), dried (MgSO4) and concentrated in vacuo to yield the title compound as pale yellow oil.

1. customThe ice bath was removed
2. stirringthe reaction mixture was stirred at room temperature overnight
3. customThe reaction mixture was partitioned between EtOAc (100 ml) and water (50 ml)
4. customThe aqueous phase was separated
5. washwashed with DCM (2×50 ml)
6. extractionback-extracted with DCM (2×100 ml)
7. washThe combined organic portions were washed with brine (50 ml)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo

ORD record

ord-969bcfdd359a4d338a21cb58333f7126

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546416B2