Triethylamine → HCID 11443343, compound

Participants

Reaction Steps

To a solution of 3-amino-4-(3-benzyloxy-5-fluoro-phenyl)-butane-1,2-diol (5.60 g, 18.34 mmol, 1.00 eq.), triethylamine (5.11 mL, 36.68 mmol, 2.00 eq.) and anhydrous DMF (100 mL) at 0° C. is added Z-glycine N-succinimidyl ester (6.18 g, 20.17 mmol, 1.10 eq.) with stirring under N2. After 2 hours, the reaction is quenched with 1N HCl, extracted with ethyl acetate, and washed with 10% NaHCO3 and then brine. The organic layer is then dried with MgSO4, filtered through Celite, and concentrated in vacuo, yielding the crude product as a light amber oil. Purification via flash chromatography in 5% MeOH/CHCl3 (rf. 0.33, KMnO4 stain), affords the final product as a white solid (5.40 g., 59% yield overall). Calculate mass for C27H29FN2O6: 496.20. Mass found for C27H29FN2O6: (OAMS) ES+: 497.5 (M+1).

Provenance & Evidence