Sodium hydride → O-(4-bromobenzyl)-N-(tert-butoxycarbonyl)-L-homoserine

Temperature

0 °C

To a flask containing Boc-L-homoserine (5.181 g, 23.63 mmol)) in THF (50 ml) was added sodium hydride (2.93 g, 73.3 mmol) and left stirring at 0° C. for 30 minutes. The reaction mixture was warmed to RT and left for 2 hrs. 4-bromo-benzylbromide (11.81 g, 47.3 mmol) was then added as a THF solution (15 ml) dropwise. The reaction was left at RT for 20 hrs. The reaction was quenched with MeOH and the solvent removed in vacuo. The residue was dissolved in water and washed with Et2O. The aqueous layer was acidified with 2M HCl and exhaustively extracted with EtOAc. The organic layer was washed with water and brine, dried over magnesium sulphate and concentrated in vacuo. The oily residue (11 g) was purified by column chromatography eluting with 50-100% EtOAc in hexanes and flushed with 10-50% MeOH in EtOAc. Yield=927 mg, 2.388 mmol, 10% yield as a viscous oil. m/z 386/388 [M−H]+.

1. waitleft
2. temperatureThe reaction mixture was warmed to RT
3. waitleft for 2 hrs
4. waitThe reaction was left at RT for 20 hrs
5. customThe reaction was quenched with MeOH
6. customthe solvent removed in vacuo
7. dissolutionThe residue was dissolved in water
8. washwashed with Et2O
9. extractionexhaustively extracted with EtOAc
10. washThe organic layer was washed with water and brine
11. dry with materialdried over magnesium sulphate
12. concentrationconcentrated in vacuo
13. customThe oily residue (11 g) was purified by column chromatography
14. washeluting with 50-100% EtOAc in hexanes
15. customflushed with 10-50% MeOH in EtOAc

ORD record

ord-a5bba22daa894ccfb68fc3c2de1316b2

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106091B2