Hydrochloric Acid → HCID 45380613, compound

Participants

Reaction Steps

To 1.0 gram of Arginyl 7-((1R,2R,3R,5S)-2-((R)-4-(2-fluorophenylthio)-3-hydroxybutyl)-3,5-dihydroxy cyclopentyl)heptanoate (8) in MeOH/H2O (4:1, 20 mL) is added, dropwise with cooling, at least 5 equivalents of a 3:1 mixture of saturated aqueous ammonium chloride and 1 M hydrochloric acid (Sigma-Aldrich, St. Louis, Mo.), and the solution is stirred for 15 minutes. Saturated aqueous sodium chloride is added along with ethyl acetate. The organic layer is separated; is washed again with brine; the solvents removed in vaccuo, and the material chromatographed to give the free acid, 7-((1R,2R,3R,5S)-2-((R)-4-(2-fluorophenylthio)-3-hydroxybutyl)-3,5-dihydroxy cyclopentyl)heptanoic acid (9).

Provenance & Evidence