(5)-tert-butyl 2-(3-(3-(2-(tert-butoxycarbonylamino)-3-((4-methoxyphenyl)(methyl)amino)-3-oxopropyl)phenyl)prop-1-enyl)-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate → (S)-2-(2-(3-(3-(2-amino-3-((4-methoxyphenyl)(methyl)amino)-3-oxopropyl)phenyl)propyl)-1H-indol-3-yl)acetic acid

Participants

Reaction Steps

A suspension of (5)-tert-butyl 2-(3-(3-(2-(tert-butoxycarbonylamino)-3-((4-methoxyphenyl)(methyl)amino)-3-oxopropyl)phenyl)prop-1-enyl)-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate (178 mg, 0.24 mmol) and palladium on carbon (134 mg, 10%) in 2.5 ml of ethanol and 2.5 ml of EtOAc, was degassed with nitrogen. The reaction was stirred at room temperature for 3 hours under an atmosphere of H2 at 1 atm. The suspension was purged with nitrogen and filtered through celite. The filtrate was concentrated and the crude product was used without further purification. MS (m/z) 728 [M+H]+. The crude product was redissolved in 1 ml of tetrahydrofuran and 1 ml of methanol and 2 ml of 2N (aq.) lithium hydroxide was added to the solution. The solution was heated at 60° C. for 2 hours. The solution was cooled in an ice bath and acidified with 1N (aq) HCl. The resulting mixture was extracted with EtOAc (2×25 ml). The organic layer was dried over Na2SO4, filtered and concentrated. TFA (2 ml) was added to the crude product. After 20 minutes, the solvent was removed and the residue was dried under high vacuum. The crude product was used without further purification. The crude product yield was (100 mg, 0.2 mmol). MS (m/z) 500 [M+H]+.

Provenance & Evidence