Tributylphosphine → (R)-N-(2,4-Dimethoxybenzyl)-5-fluoro-3-(1-(2-iodophenyl)ethyl)-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

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Reaction Steps

Added N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (11-3, 2 g, 4.29 mmol) to THF (21.44 ml). Added tri-n-butylphosphine (2.116 ml, 8.58 mmol) and DEAD (1.358 ml, 8.58 mmol) and cooled to 0° C. Was a clear orange solution. Added (S)-1-(2-iodophenyl)ethanol (16-2, 1.064 g, 4.29 mmol). After 24 h at 0° C., concentrated in vacuo, dissolved in 5 mL DCM and purified by normal-phase HPLC (80 g ISCO column, 0-50% EtOAc:Hex) to give 32-1 as a white solid.

Provenance & Evidence