9-Fluorenylmethyl chloroformate → (4-Acetylamino-3-benzyloxy-phenyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Participants

Reaction Conditions

Reaction Steps

N-(4-Amino-2-benzyloxy-phenyl)-acetamide (419) (3 g, 11.72 mmol) and Fmoc-Cl (3.1 g, 12 mmol) were combined and dissolved in THF (60 mL). iPr2EtN (18 mmol, 1.2 equiv.) was added and the mixture was heated to 80° C. for 15 minutes while stirring. TLC indicated complete reaction at this point. The mixture was poured into ice-water (500 mL) and a white solid precipitated. The solid was collected by filtration under reduced pressure followed by drying under high vacuum to give the desired product (420) as a white powder (3 g, 6.28 mmol, 54% yield). LC-MS (ESI): (exact mass: 478.19) m/e=479.2 [M+1]+ (70%), 957.6 [2M+1]+ (100%).

Provenance & Evidence