Tetrabutylammonium Fluoride → HCID 86587957, compound

Participants

Reaction Steps

A solution of tert-butyl (5S,12S)-12-[(R)-[(3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-5-[(1S)-1-hydroxyethyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (63 mg, 0.062 mmol, obtained from Example 10) in anhydrous tetrahydrofuran (1 ml) was cooled at 0° C. under nitrogen. Tetrabutylammonium fluoride (0.186 mL, 0.186 mmol; 1 M solution in tetrahydrofuran, Aldrich) was added and the resulting mixture was warmed to room temperature and stirred for 2.75 hours. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (flash column, silica gel, 5% methanol in methylene chloride) to provide tert-butyl (5S,12S)-12-[(R)-[(3S,4R,5R)-3,4-dihydroxy-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-(hydroxy)methyl]-5-[(1S)-1-hydroxyethyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (12 mg, 25%) as a light yellow solid.

Provenance & Evidence