Diisopropylethylamine → HCID 178468200, compound

Participants

Reaction Steps

4-(3-{4-[(2S)-2-Carboxy-2-ethoxyethyl]phenoxy}propyl)benzenaminium chloride (152 mg, 0.4 mmol) was in isopropyl alcohol (3 ml). N,N-diisopropylethylamine (0.28 ml, 1.6 mmol) was added. The mixture was stirred for 5 minutes, then 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (290 mg, 0.4 mmol) was added. The mixture was stirred at room temperature for 7 days and thereafter evaporated in vacuum to dryness. Water and ethyl acetate were added into the residue. The mixture was acidified with 1% hydrochloric acid, pH˜5 and there was some precipitation. The two phase mixture was filtered and then separated. The pH of the water phase was further adjusted to ˜3 and the water phase was extracted with ethyl acetate (×2). All organic phases were combined and washed with brine and dried with magnesium sulfate. The solvent was evaporated in vacuum. Chromatography of the residue on an ISOLUTE column (SI, 2 g/6 ml) using heptane/DCM (50:50), then DCM and MeOH/DCM (0.5: 99.5) as eluant gave the desired product (63 mg), yield 27%.

Provenance & Evidence