Hydrochloric Acid → HCID 90289965, compound

Participants

Reaction Steps

To a solution of (S)—S-3-(2-(tert-butoxycarbonylamino)-3-((4-methoxyphenyl)(methyl)amino)-3-oxopropyl)phenyl ethanethioate (335 mg, 0.73 mmol) in ethanol (2 ml) was added potassium hydroxide (82 mg, 1.46 mmol). After 10 minutes, ethyl 2-(1-acetyl-2-(bromomethyl)-1H-indol-3-yl)acetate (I-4A, 272 mg, 0.8 mmol) was added. The reaction was stirred for 2 hours and then neutralized with 1N (aq) HCl then extracted with EtOAc. The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (1-5% MeOH/DCM) to provide the desired product (347 mg, 0.55 mmol), 75.3%. MS (m/z) 632 [M+H]+.

Provenance & Evidence