1,2-Dichloroethane → N-(2-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-2-oxoethyl)-2-(5-formylthiazol-2-ylamino)-3-methylbutanamide

Participants

Reaction Steps

Following the procedure described in Example 4, except using the material from Example 20 (77 mg, 0.169 mmol), glycyl-L-tyrosinamide hydrochloride (159.5 mg, 0.583 mmol), EDC (190.3 mg, 0.993 mmol), 1-hydroxy-7-azabenzotriazole (29 mg, 0.213 mmol), anhydrous DMF (4 mL) and N-methylmorpholine (350 μL, 3.18 mmol), 86.7 mg (41%) of the title compound is obtained as an orange solid as a TFA salt. Purification is done 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=6.82-6.69 min. LC/MS (Condition A): ret. T=2.11-2.18 min, (M+H)+ 448.18.

Provenance & Evidence