Phenethyl bromide → HCID 86760293, compound

Participants

Reaction Steps

To a CH3CN (50 mL) solution containing methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-mercapto-3-methylbutanoate (as described above) (1.26 g, 4.78 mmol, 1.0 eq) was added sodium tert-butoxide (597 mg, 6.21 mmol, 1.3 eq). The resulting pale yellow mixture was allowed to stir at RT for 10 min at which time (2-bromoethyl)benzene (718 μL, 5.26 mmol, 1.1 eq) was added. The resulting solution was allowed to stir at RT for 18 hr. The reaction was then quenched with a sat NH4Cl solution, poured into H2O, and extracted (2×) with EtOAc. Combined extracts were dried over MgSO4 and concentrated in vacuo. Purified via flash chromatography using 5:1 hexanes/EtOAc as the mobile phase. Isolated 761 mg (2.07 mmol, 45% yield).

Provenance & Evidence