Hydrochloric Acid → (S)-ethyl 2-(2-((3-(2-(tert-butoxycarbonylamino)-3-((4-methoxyphenyl)(methyl)amino)-3-oxopropyl)benzylthio)methyl)-1H-indol-3-yl)acetate

Participants

Reaction Steps

To a solution 2-(1-acetyl-2-(acetylthiomethyl)-1H-indol-3-yl)acetate (392 mg, 1.17 mmol) in ethanol (10 ml), was added potassium hydroxide (0.13 g, 2.32 mmol). After 10 minutes, (S)-tert-butyl 3-(3-(chloromethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (507 mg, 1.17 mmol) was added to the solution. The reaction was stirred for 2 hours and then neutralized with 1N (aq) HCl. The mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (3-6% MeOH/DCM) to provide the desired product (650 mg, 1.0 mmol), 85%. MS (m/z) 646 [M+H]+.

Provenance & Evidence