4-Methylmorpholine → HCID 10223276, compound

A solution of (3R)-6-cyclohexyl-3-(3-{[(2-methoxy-2-oxoethyl)(methyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoic acid (Preparation 39) (273 mg, 0.70 mmol)and N-methylmorpholine (85 μl, 0.77 mmol) in anhydrous dichloromethane (10 ml) was cooled to 0° C., treated with isobutyl chloroformate (100 μl, 0.77 mmol) and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. O-(Trimethylsilyl)hydroxylamine (250 μl, 2.10 mmol) was then added and the mixture stirred under a nitrogen atmosphere for 1 hour, being allowed to warm to room temperature over this time. The mixture was then quenched with methanol (10 ml) and stirred for 10 minutes. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The layers were separated and the organic layer was sequentially washed with water and brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by HPLCa to afford the title compound as a colourless oil (187 mg).

1. stirringthe mixture stirred under a nitrogen atmosphere for 1 hour
2. customThe mixture was then quenched with methanol (10 ml)
3. stirringstirred for 10 minutes
4. customThe solvent was removed under reduced pressure
5. customthe residue partitioned between ethyl acetate and water
6. customThe layers were separated
7. washthe organic layer was sequentially washed with water and brine
8. dry with materialdried over anhydrous sodium sulphate
9. filtrationfiltered
10. customthe solvent removed under reduced pressure
11. customThe residue was purified by HPLCa

ORD record

ord-5aa7ed9230d04055b2bb88d8fe4aa598

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06897306B2