Diphenylacetic Acid → HCID 86751164, compound

Participants

Reaction Steps

A solution of 0.94 g (2.7 mmol) of (R,S; R,S)-2-amino-3-(3-methoxyphenyl)-3-(3-methoxyphenyl-sulfanyl)propionic acid, methyl ester of Example 32, 15 mL of methylene dichloride, 0.69 g (3.2 mmol) of diphenylacetic acid, 0.62 g (3.2 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDAC), and 0.02 g (0.16 mmol) of 4-dimethylaminopyridine (DMAP) is stirred at room temperature for 18 hours. The reaction solution is diluted with 100 mL of methylene dichloride, washed with 80 mL of 1N sodium hydroxide and then 80 mL of 1N hydrochloric acid, dried (magnesium sulfate), and evaporated. The residue is purified via silica gel chromatography eluting with 25% ethyl acetate-hexane to give the product as an inseparable mixture of diastereomers; wt 1.10 g (90%);

Provenance & Evidence