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

Participants

Reaction Steps

To a solution ethyl 2-(2-(acetylthio)-1H-indol-3-yl)acetate (380 mg, 1.4 mmol) in ethanol (5 ml) was added potassium hydroxide (84 mg, 1.5 mmol). After 10 minutes, (5)-tert-butyl 3-(3-(chloromethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (I-5, 605 mg, 1.4 mmol) was added to the solution. The reaction was stirred for 2 hours and then neutralized with 1N (aq) HCl and then 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 (1-5% MeOH/DCM) to provide the desired product (796 mg, 1.26 mmol), 90%. MS (m/z) 632 [M+H]+.

Provenance & Evidence