Sodium Bicarbonate → HCID 178450926, compound

Participants

Reaction Steps

4-Carbamimidamidobenzoyl chloride hydrochloride (77 mg) was added to a mixture of tert-butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(3-(3-tert-butoxy-3-oxopropyl)-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (167 mg), pyridine (0.16 mL), and NMP (0.16 mL) at 50 C, and the obtained mixture was stirred at 50 C for 30 minutes. Further, 4-carbamimidamidobenzoyl chloride hydrochloride (77 mg) was added thereto, and the obtained mixture was stirred at 50 C for 3 hours. Pyridine (0.16 mL) and NMP (0.16 mL) were added thereto, then 4-carbamimidamidobenzoyl chloride hydrochloride (77 mg) was added, and then, the obtained mixture was stirred at 50 C for 30 minutes. Further, 4-carbamimidamidobenzoyl chloride hydrochloride (77 mg) was added thereto, and the obtained mixture was stirred overnight at 50 C. The reaction mixture was fractionated by HPLC (C18, mobile phase: water/acetonitrile (system containing 0.1% TFA)). To the obtained fraction, a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (104 mg).

Provenance & Evidence