Dicyclohexylcarbodiimide → methyl 2-(2-(4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetamido)-2-methylpropanoate

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 2-(4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetic acid 354 (15 mg, 0.02 mmol), methyl 2-amino-2-methylpropanoate (3.6 mg, 0.03 mmol) and HOBt (3.03 mg, 0.02 mmol) in anhydrous DMF (0.5 mL) was added dicyclohexyl carbodiimide (DCC) (4.6 mg, 0.02 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and allowed stir at room temperature for 36 h. The reaction was quenched with saturated NaHCO3 (2 mL) then extracted with EA (2×3 mL). The combined organic extract was washed with brine (5 mL), dried (MgSO4), filtered and concentrated to afford methyl 2-(2-(4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-(5-(4′-methyl-[1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetamido)-2-methylpropanoate INT-72 which was used in the next step without purification. LCMS-ESI (m/z) calculated for C46H42F3N5O7: 834; no ion observed, tR=4.44 min (Method 3).

Provenance & Evidence