Tetrabutylammonium Fluoride → HCID 178470375, compound

Participants

Reaction Steps

6-tert-Butyloxy-9-{5-[5-(tert-butyl-dimethyl-silanyloxy)-1H-benzimidazol-2-ylsulfanyl]-furan-2-yl}-8-oxo-2,4,5,7,8,9-hexahydro-pyrrolo[3,4-b]-1,7-naphthyridine-3-carboxylic acid ethyl ester (0.5 g, 0.71 mmol) is treated with tetra-N-butylammonium fluoride (0.185 g, 0.71 mmol) in tetrahydrofuran (5 ml) for 4 hours at room temperature. The reaction mixture is concentrated under reduced pressure and the residue is purified on a silica gel column (40 g) eluted with a mixture of dichloromethane and methanol (9/1, v/v). The fractions containing the expected product are concentrated under reduced pressure and the solid obtained is washed with actonitrile (30 ml), pentane (30 ml) and dried under vacuum to yield 270 mg of 6-tert-butyloxy-9-[5-(5-Hydroxy-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-2,4,5,7,8,9-hexahydro-pyrrolo[3,4-b]-1,7-naphthyridine-3-carboxylic acid ethyl ester. Yield=64%. Analytical LC/MS (method B): retention time=3.34 min., m/z=592.31 (positive ion mode).

Provenance & Evidence