Water → (4-Hydroxycyclohexyl)acetic acid

Temperature

0 °C

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)+.

1. filtrationThe reaction mixture was filtered through Celite
2. washwashed with dioxane
3. filtrationfiltered
4. concentrationconcentrated to 20 mL
5. additionAn additional 20 mL of dioxane was added
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in water and neutralized with 1N HCl to pH 2-3
8. filtrationThe precipitated white solid was filtered

ORD record

ord-533f2a3b394c45608b1536359ee887c1

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06716833B2