Ethyl Acetate → HCID 53759858, compound

Participants

Reaction Steps

5-Indanol (52.9 mg, 0.394 mmol) is added in one portion to a solution of (S)-N-[2-(diphenylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionic acid (200 mg, 0.394 mmol) in methylene chloride (25 ml). 4-(N,N-Dimethylamino)pyridine (48.1 mg, 0.394 mmol) is added followed by N-dimethylaminopropyl-N'-ethylcarbodiimide hydrochloride (151 mg, 0.788 mmol). The solution is stirred at room temperature for 3 hours. Ethyl acetate (60 mL) and water (15 mL) are added. The organic layer is subsequently washed with a saturated solution of sodium bicarbonate (2×15 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel, eluting with ethyl acetate-hexane (1:1). Evaporation of the pure fraction yields 5-indanyl (S)-N-[2-(diphenylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionate, as a thick colorless oil that can be crystallized from ether, m.p. 89°-91°.

Provenance & Evidence