Tetrabutylammonium Fluoride → HCID 86590885, compound

Participants

Reaction Steps

To a solution of (2S)-2-{[3-(benzoyloxy)-azetidine-1-carbothioyl]amino}-3-(t-butyldiphenylsilyloxy)propionic acid methyl ester (23.3 g, 40.0 mmol) (obtained as described in Reference Example 70(3)) in tetrahydrofuran (700 ml) was added a 1.0 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (48.4 g, 48.4 mmol) in an ice bath and the mixture was stirred overnight. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:acetonitrile (3:1) as the eluant to afford (2S)-2-{[3-(benzoyloxy)-azetidine-1-carbothioyl]amino}-3-hydroxy-propionic acid methyl ester (12.6 g, yield 92%) as a white solid.

Provenance & Evidence