Bromide ion → HCID 57857123, compound

Participants

Reaction Steps

To a solution of tert-butyl [2-[(4-aminobenzoyl)amino]-4-(3-thienyl)phenyl]carbamate (945 mg, 2.31 mmol) in CH3CN (5.0 mL) was added K2CO3 (639 mg, 4.62 mmol), tert-butyl bromoacetate (1.35 mL, 9.24 mmol), and NaI (139 mg, 0.92 mmol). The reaction mixture was heated at reflux for 12 hours and an additional portion of bromide and NaI were added to obtain mono and bis alkylated product. The reaction was cooled to room temperature, filtered and the organic layer was concentrated in vacuo. The crude residue was purified by reverse-phase chromatography (10-100% MeCN/H2O with 0.05% TFA) to separate mono and bis alkylated product (ratio of mono to bis is ˜1:2). The appropriate fractions were combined, diluted with EtOAc (20 mL) and washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo and gave the desired tert-butyl {[4-({[2-[(tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)phenyl]amino}acetate which was confirmed MS: cal'd 524.2 (MH+), exp 524.2 (MH+).

Provenance & Evidence