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

Participants

Reaction Conditions

Reaction Steps

Accordingly, the compound of Formula 28-1 ((R)-3-(1-(3-bromophenyl)ethyl)-N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide) was prepared from a solution provided by dissolving 2 g of the compound of Formula 11-3 (4.29 mmol, prepared as described above) and 0.862 g of (S)-1-(3-bromophenyl)ethanol (4.29 mmol) in 10 mL of THF. This solution was cooled to 0° C. and treated with triphenylphosphine (2.25 g, 8.58 mmol) followed by DEAD (1.36 mL, 8.58 mmol). After stirring at 0° C. for 120 min, the reaction mixture was diluted with EtOAc (50 mL) and sat'd sodium bicarbonate (10 mL), the aqueous layer was extracted with EtOAc (2×20 mL). The combined organics were washed with brine (10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by normal phase chromatography (10-80% EtOAc in hexane) yielded the compound of Formula 28-1 as a solid which was used as isolated.

Provenance & Evidence