Water → (4-Hydroxycyclohexyl)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of D-4-hydroxy phenylglycine dissolved in 3N NaOH was added Raney nickel (6.75 g) and water (45 mL) and the mixture was then hydrogenated on a Parr hydrogenator at 50-80° C. for 24 h at 40 psi of hydrogen. The reaction mixture was filtered through Celite, washed with dioxane, filtered and concentrated to 20 mL. An additional 20 mL of dioxane was added and the reaction was cooled to 0° C. and triethylamine (2.72 mL, 19.4 mmol) was added, followed by 4-(2-butynyloxy)-benzenesulfonyl chloride (3.21 g, 13.2mmol). The mixture was stirred at room temperature overnight and then concentrated in vacuo. The residue was dissolved in water and neutralized with 1N HCl to pH 2-3. The precipitated white solid was filtered to provide 2.8 g of (2R)-{[4-(2-butynyloxy)phenyl]sulfonyl}amino)(4-hydroxycyclohexyl)ethanoic acid. mp 90-100° C. Electrospray Mass Spec 382.1 (M+H)+.

Provenance & Evidence