Ethanol → HCID 9872387, compound

Participants

Reaction Steps

(2R,3S)-3-(4-Methyl-benzyloxy)-2-(4′-methylsulfanyl-biphenyl-4-sulfonylamino)-3-thiazol-2-yl-propionic acid methyl ester. The (2R,3S)-2-(4-bromo-benzenesulfonylamino)-3-(4-methyl-benzyloxy)-3-thiazol-2-yl-propionic acid methyl ester 1e (660 mg, 1.26 mmol) and 4-thiomethoxyphenylboronic acid (320 mg, 1.88 mmol) are taken up in 10 mL of benzene, 1.5 mL of EtOH and 1.5 mL of water in the presence of Pd(PPh3)4 (44 mg, 0.03 mmol) and 267 mg of Na2CO3 and brought to reflux for 4 hours. The mixture is cooled to room temperature, poured into water, and extracted with methylene chloride. The organic layer is dried over Na2SO4, filtered and evaporated. The crude product is purified by silica gel chromatography using 8/2 hexane/EtOAc to give the desired product as a colorless oil.

Provenance & Evidence