Diisopropylethylamine → Ethyl {3-[4-({[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]-3-oxopropyl}methylphosphinate

Participants

Reaction Steps

4-{3-[(ethyloxy)(methyl)phosphoryl]propanoyl}benzoic acid (1 g, 3.52 mmol), 1,1-dimethylethyl [2-amino-4-(2-thienyl)phenyl]carbamate (1.532 g, 5.28 mmol), DIPEA (0.922 mL, 5.28 mmol) and BOP (2.334 g, 5.28 mmol) were stirred in DMF (10 mL) at room temperature overnight. Saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with water and brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by MPLC (0-20% MeOH-EtOAc) gave ethyl {3-[4-({[2-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]-3-oxopropyl}methylphosphinate as an orange solid. MS: cal'd 457 (MH+-Boc), exp 457 (MH+-Boc).

Provenance & Evidence