N-bromobutanimide → methyl 4-[(1S)-1-({[5-bromo-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

Participants

Reaction Steps

N-Bromosuccinimide (43.0 mg, 0.242 mmol) was added to methyl 4-[(1S)-1-({[4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate from Example 3, Step 4 (50.0 mg, 0.121 mmol) in 1:1 CH2Cl2/AcOH (1.2 mL). After 16 h, the reaction was slowly poured in 5% aq. NaHCO3. The aqueous layer was extracted with CHCl3 and the combined organics were washed with 5% aq. NaHCO3, sat. Na2S2O3 and brine, dried (Na2SO4) and concentrated. The crude product was purified by Combi Flash chromatography system (0-2% EtOAc/CHCl3 in 15 min.) to afford the desired product as a brown solid.

Provenance & Evidence