Methanol → HCID 16748901, compound

A solution of (3R)-6-cyclohexyl-3-[3-(3-pyridinylmethyl)-1,2,4-oxadiazol-5-yl]hexanoic acid (Preparation 109) (410 mg, 1.04 mmol) in dichloromethane (10 ml) was treated with 1,1′-carbonyidiimidazole (169 mg, 1.04 mmol) and stirred under a nitrogen atmosphere for 1 hour. O-(Trimethylsilyl)hydroxylamine (418 μl, 3.12 mmol) was added and the reation mixture was stirred for 18 hours. The reaction mixture was then treated with methanol (5 ml) and stirred at room temperature for 3 hours. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with water (3×30 ml) and brine, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 (dichloromethane:methanol) gradually changing to 95:5 (dichloromethane:methanol) to afford a white waxy solid. The solid was recrystallised from ethyl acetate to afford the title compound as a white solid (128 mg).

1. stirringthe reation mixture was stirred for 18 hours
2. stirringstirred at room temperature for 3 hours
3. customThe solvent was removed under reduced pressure
4. dissolutionThe residue was dissolved in ethyl acetate
5. washwashed with water (3×30 ml) and brine
6. dry with materialdried over anhydrous magnesium sulphate
7. filtrationfiltered
8. customthe solvent removed under reduced pressure
9. customThe residue was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 (dichloromethane:methanol)
10. customto afford a white waxy solid
11. customThe solid was recrystallised from ethyl acetate

ORD record

ord-25c0025625be4192a0c63bb94db72701

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06448278B2