2,6-Lutidine → HCID 10135702, compound

A solution of (3R)-6-cyclohexyl-3-{3-[(propylsulfonyl)methyl]-1,2,4-oxadiazol-5-yl}hexanoic acid (Preparation 97) (298 mg, 0.77 mmol) and 2,6-lutidine (135 μl, 1.16 mmol) in dichloromethane (10 ml) was cooled to 0° C., treated with isobutyl chloroformate (100 μl, 0.77 mmol) and stirred under a nitrogen atmosphere for 1 hour. O-(Trimethylsilyl)hydroxylamine (310 μl, 2.31 mmol) was added and the mixture was stirred for 4 hours, being allowed to warm to room temperature over this time. The mixture was then treated with methanol (5 ml) and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with hydrochloric acid (1 M) and brine, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The oil was purified by column chromatography on silica gel eluting with a gradient system of 100:0 (dichloromethane:methanol) gradually changing to 95:5 (dichloromethane:methanol) to afford the title compound as a white solid (140 mg).

1. stirringthe mixture was stirred for 4 hours
2. stirringstirred at room temperature for 1 hour
3. customThe solvent was removed under reduced pressure
4. dissolutionThe residue was dissolved in ethyl acetate
5. washwashed with hydrochloric acid (1 M) and brine
6. dry with materialdried over anhydrous magnesium sulphate
7. filtrationfiltered
8. customthe solvent removed under reduced pressure
9. customThe oil was purified by column chromatography on silica gel eluting with a gradient system of 100:0 (dichloromethane:methanol)

ORD record

ord-08a519a7cdaa44119513ba21162e2e7a

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06897306B2