4-({[5-(Tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethylamine → (2S)-1-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-3-{[4-({[5-(tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-2-propanol

Participants

Reaction Conditions

Reaction Steps

A solution of the amine of Example 13 (0.873 g, 2.70 mmol) and tert-butyl{4-[(2S)oxiranylmethoxy]phenoxy}diphenylsilane (0.980 g, 2.42 mmol) in a mixture of methanol (20 mL) and THF (3 mL) was heated to 45° C. for 23 h. TLC shows characteristic product spot at Rf=0.25(silica gel plate; dichloromethane/chloroform/methanol: 20/5/2). The reaction mixture was cooled, silica gel (5 g) was added and the methanol was remove in vacuo. The reaction mixture, preabsorbed onto silica gel was applied to the top of a flash chromatography column (silica gel; dichloromethane/chloroform/methanol: 12/3/1) and purified in the standard manner. This procedure afforded 0.660 g of the title compound as a white foam.

Provenance & Evidence