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

Participants

Reaction Steps

To a mixture of material from Example 3 (32.2 mg, 0.107 mmol), (S)-2-amino-N-((S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)propanamide (42.7 mg, 0.170 mmol), EDC (31.7 mg, 0.165 mmol) and 1-hydroxy-7-azabenzotriazole (10.0 mg, 0.073 mmol) is added anhydrous DMF (1.0 mL). The reaction is flushed with N2, treated with N-methylmorpholine (59 μl, 0.537 mmol), flushed with N2 and allowed to stir at room temp for 18 h. The reaction is diluted with DMF 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 12 min, ret. T=5.2 min. The product fractions are evaporated to dryness in a speed-vac for 18 h to give 26.7 mg (46.7%) of the title compound as a yellow solid as a TFA salt. LC/MS (Condition A): ret. T=1.65 min, (M+H)+ 420.09.

Provenance & Evidence