Diisopropylethylamine → HCID 56953688, compound

Participants

Reaction Steps

Step (c) DIEA (0.88 mL, 5.10 mmol) and HATU (750 mg, 2 mmol) were added to a stirred solution of 4-(4-fluorophenoxy)benzene-1,2-diamine (370 mg, 1.7 mmol), (S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid (550 mg, 1.86 mmol) and DMF (4 mL) at ambient temperature. The mixture was stirred for 1 hour and then aqueous saturated sodium bicarbonate solution (8 mL) was added. The resulting solution was extracted with ethyl acetate (4×2 mL) and the combined extract was dried over magnesium sulfate and concentrated. Product was purified from the residue by silica gel column chromatography (eluting with a 3:1→2:1 mixture of hexane/EtOAc) to give (S)-tert-butyl 1-(2-amino-4-(4-fluorophenoxy)phenylamino)-3-(benzyloxy)-1-oxo-propan-2-ylcarbamate (610 mg, 72%) as a brown foam.

Provenance & Evidence