Diisopropylethylamine → (5)-tert-butyl 2-allyl-3-(2-(3-(3-iodophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylamino)-2-oxoethyl)-1H-indole-1-carboxylate

Participants

Reaction Steps

A solution of (S)-tert-butyl 3-(3-iodophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (556 mg, 1.09 mml) in TFA (3 ml) was stirred for 10 minutes. The solvent was removed in vacuo. 2-(2-allyl-1-(tert-butoxycarbonyl)-1H-indol-3-yl)acetic acid (343 mg, 1.09 mmol), DIEA (0.38 ml, 2.18 mmol) and O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 414.4 mg, 1.09 mmol) were dissolved in DMF. After 10 minutes, the solution was added to TFA salt. The reaction was stirred for 2 hours at room temperature. The mixture was diluted with EtOAc (100 ml) and washed with brine (2×50 ml). The organic layer was dried over Na2SO4, filtered and concentrated. The oily crude product was introduced to a silica gel loading column and purified by column chromatography (20-50% EtOAc/hexanes) to provide the desired product (620 mg, 0.94 mmol. MS (m/z) 660 [M+H]+.

Provenance & Evidence