1,2-Dichloroethane → (S)-N-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-2-((S)-2-(2-(5-formylthiazol-2-ylamino)acetamido)propanamido)propanamide

Participants

Reaction Steps

To a mixture of material from Example 3 (62 mg, 0.207 mmol), 1-hydroxy-7-azabenzotriazole (7.2 mg, 0.126 mmol), and (S)-2-amino-N-((S)-1-((S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)propanamide (53.8 mg, 0.167 mmol) in anhydrous DMF (2.0 mL) is added sequentially N-methylmorpholine (125 μL, 1.137 mmol) and EDC (51.8 mg, 0.270 mmol). The resulting solution is stirred at room temperature for 6 h, diluted with MeOH (8 mL) and purified by preparative HPLC (Condition A) using a PHENOMENEX® Luna Axia 30×100 mm S10 column from 10% Solvent B to 80% Solvent B over 11 min, ret. T=4.19-5.20 min. The fractions containing the desired product were evaporated to dryness to give 42.4 mg (34%) of the title compound as a yellow solid as a TFA salt. LC/MS (Condition A): ret. T=1.81 min, (M+H)+ 491.15.

Provenance & Evidence