Sodium Thiosulfate → methyl 4-[(1S)-1-({[2,5-dichloro-4-(3-chlorobenzoyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

Participants

Reaction Steps

Dess-Martin periodinane (114 mg, 0.268 mmol) was added to methyl 4-{(1S)-1-[({2,5-dichloro-4-[(3-chlorophenyl)(hydroxy)methyl]-3-thienyl}carbonyl)amino]ethyl}benzoate from Example 9, Step 1 (89.0 mg, 0.178 mmol) in CH2Cl2 (1.5 mL). After 17 h, the suspension was poured in 20 mL of sat. NaHCO3 containing 7 eq of Na2S2O3 and stirred for 10 min., after which clear layers were obtained. The aqueous layer was extracted with CHCl3, and the combined organics were washed with 5% aq. NaHCO3, water and brine, dried (Na2SO4) and concentrated. The crude product was purified by Combi Flash chromatography system (2-8% EtOAc/toluene in 20 min.) to afford the desired product as a white solid.

Provenance & Evidence