Hydroxylamine → 3-([1,1'-biphenyl)-4-ylsulfonyl)-N-[3-phenoxy-1-phenylpropyl]-1,3-thiazolidine-2-carboxamide

Participants

Reaction Steps

Thiazolidine intermediates of general structure (XXVI), e.g., 3-([1,1′-biphenyl]-4-ylsulfonyl)-N-(3-hydroxy-1-phenylpropyl)-1,3-thiazolidine-2-carboxamide (1.0 g, 1.0 eq, 2.07 mmol) was dissolved in 20 ml dry THF under nitrogen. Phenol (252 mg, 1.5 eq, 2.69 mmol), diethylazodicarboxylate (470 mg, 1.5 eq, 2.69 mmol) and triphenyl phosphine polymer bound (1.0 g, 1.5 eq, 2.70 mmol) were then added and the reaction mixture was shaken for 12 hours at RT. Triphenyl phosphine resin was filtered off and the THF solution evaporated in vacuo. The residue was taken up in DCM and washed twice with saturated sodium carbonate solution and then water. The organic layer was dried with magnesium sulfate and concentrated in vacuo to give a crude product which was purified on silica gel using cyclohexane/ethyl acetate(8/2) as eluent, affording the desired products of general structure (XXVII), e.g., 3-([1,1′-biphenyl]-4-ylsulfonyl)-N-[3-phenoxy-1-phenylpropyl]-1,3-thiazolidine-2-carboxamide as a white oil in 40% yield and 95.5% purity by HPLC.

Provenance & Evidence