Tetrabutylammonium Fluoride → 4-({(2S)-3-[(4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethyl)amino]-2-hydroxypropyl}oxy)phenol

Participants

Reaction Steps

To a solution of the amino alcohol of Example 23 (0.490 g, 0.643 mmol) in THF (10 mL) was added a 1M solution of TBAF (0.13 mL, 0.13 mmol). The reaction mixture was stirred for 6 h. TLC shows the absence of starting material, so 3 drops of a saturated aqueous ammonium chloride solution was added. The reaction mixture was evaporated in vacuo to dryness and the residue was flash chromatographed (silica gel; dichloromethane/chloroform/methanol: 5/4/1) to afford 0.211 g of the title compound as a white crystalline solid. MP=51-57° C.

Provenance & Evidence