Ethanol → HCID 86754115, compound

Participants

Reaction Steps

(1S, 2R, 3R, 5R)-3-Acetoxymethyl)-5-(2-bromo-5,6-dichloro-1-H-benzimidazol-1-yl)-1,2-cyclopentanediyl diacetate (500 mg 0.958 mmole) was refluxed in water: ethanol/2:1 (7.5 mL) with cyclopropylamine (0.66 mL, 9.6 mmole) under nitrogen for 18 hours. TLC (silica gel, 10% methanol-chloroform) showed complete conversion to a single spot with lower Rf than starting material. 1 N sodium hydroxide (0.96 mL) was added and volatiles were evaporated. The residue was chromatographed on a silica gel flash column. Title compound was eluted with 10% methanol-chloroform as a colorless glass which solidified from water:ethanol/2:1 (5 mL) to give off-white powder (207 mg, 59%, m.p. 116-118° C. dec.; 1H-NMR(DMSO-d6)δ and mass spectrum: identical with those of enantiomer described in Example 74; [α]20589 -12.2°, [α]20578 -12.5°, [α]20546 -13.5° (c=0.312, methanol).

Provenance & Evidence