Sodium Hydroxide → HCID 86587109, compound

Participants

Reaction Steps

To a solution of tert-butyl(dimethyl)silyl(2R)-){[4-(2-butynyloxy)phenyl]sulfonyl}amino)(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)ethanoate (0.76 g, 1.24 mmol) in 8 mL of THF/methanol (1:1) was added 1 N NaOH (1.25 mL, 1.25 mmol) and the reaction was stirred at room temperature overnight. Reducing the solvent to one quarter volume, then adding brine, the aqueous layer was neutralized with 1M KHSO4 to pH˜4 and then extracted with ethyl acetate. The combined organics were washed with water and brine, dried over sodium sulfate, filtered, and concentrated to obtain 0.68 g of (2R)-{[4-(2-butynyloxy)phenyl]sulfonyl)amino)(4-{[tert-butyl-(dimethyl)silyl]oxy}cyclohexyl)ethanoic acid. Electrospray Mass Spec 494.2 (M−H)−.

Provenance & Evidence