1,2-Dichloroethane → (S)-N-((S)-1-((S)-1-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)-1-(5-formylthiazol-2-yl)pyrrolidine-2-carboxamide

Participants

Reaction Steps

To a solution of material from Example 80 (25 mg, 0.110 mmol), (S)-2-amino-N-((S)-1-((S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)propanamide, TFA (25 mg, 0.057 mmol), and 1-hydroxy-7-azabenzotriazole (4 mg, 0.029 mmol) in anhydrous DMF (2 mL) is added sequentially EDC (12 mg, 0.063 mmol), followed by N-methylmorpholine (40 μl, 0.364 mmol). The resulting solution is stirred at room temp for 45 min, diluted with MeOH (5 mL) and purified by preparative HPLC (Condition A) using a PHENOMENEX® Luna Axia 30×100 mm S10 column from 15% Solvent B to 85% Solvent B over 11 min, ret. T=5.9 min. The fractions containing the desired product were evaporated to dryness to give 23 mg (63%) of the title compound as a white solid as a TFA salt. LC/MS (Condition A): ret. T=2.04 min, (M+H)+ 531.27.

Provenance & Evidence