HCID 131732754, compound → HCID 131732753, compound

Participants

Reaction Steps

(S)-ethyl 2-(2-(3-(2-(tert-butoxycarbonylamino)-3-((4-chlorophenyl)(methyl)amino)-3-oxopropyl)styryl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)acetate (170 mg, 0.26 mmol) was dissolved in 50 mL of ethyl acetate and purged with nitrogen. Rhodium (5 wt. % on alumina powder, 60 mg) was added. The reaction mixture was purged with hydrogen and stirred at ambient temperature overnight under a hydrogen balloon. After completion of the reaction, the mixture was filtered, rinsing with ethyl acetate. The filtrate was concentrated to afford (S)-ethyl 2-(2-(3-(2-(tert-butoxycarbonylamino)-3-((4-chlorophenyl)(methyl)amino)-3-oxopropyl)phenethyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)acetate which was dissolved in 5 mL of THF/MeOH/H2O (3/2/1), and to it was added LiOH.H2O (55 mg). The reaction mixture was allowed to stir at ambient temperature for two hours and then purified by RP HPLC eluting with acetonitrile/water (with 0.1% TFA) to afford (S)-2-(2-(3-(2-(tert-butoxycarbonylamino)-3-((4-chlorophenyl)(methyl)amino)-3-oxopropyl)phenethyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)acetic acid. The compound was dissolved in 3 mL of 10% TFA/CH2Cl2 and stirred at ambient temperature for two hours. The reaction was cooled down to 0° C. and quenched with 0.3 mL of pyridine. The solvent was removed and the residue was purified by RP HPLC eluting with acetonitrile and water to afford 106 mg of (S)-2-(2-(3-(2-amino-3-((4-chlorophenyl)(methyl)amino)-3-oxopropyl)phenethyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)acetic acid. MS (m/z): 521.3 [M+H]+; HPLC retention time 2.05 min (5-99% acetonitrile:water with 0.05% formic acid).

Provenance & Evidence