4-Methylmorpholine → HCID 10159338, compound

A solution (3R)-6-cyclohexyl-3-(3-{[[3-(dimethylamino)propyl](methyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoic acid (Preparation 84) (566 mg, 0.88 mmol) and N-methylmorpholine (390 μl, 3.52 mmol) in dichloromethane (10 ml) was cooled to 0° C., treated with isobutyl chloroformate (340 μl, 2.64 mmol) and stirred under an argon atmosphere for 1 hour. O-(Trimethylsilyl)hydroxylamine (540 μl, 4.40 mmol) was added and the mixture was stirred for 4.5 hours, being allowed to warm to room temperature over this time. The mixture was then treated with methanol (2.5 ml) and stirred at room temperature for 20 minutes. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (100 ml) and washed with water (20 ml), dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The solid was purified by column chromatography on silica gel eluting with a gradient system of 97:3:0.3 (dichloromethane:methanol:ammonia) gradually changing to 90:10:1 (dichloromethane:methanol:ammonia) to afford the title compound (150 mg).

1. stirringthe mixture was stirred for 4.5 hours
2. stirringstirred at room temperature for 20 minutes
3. customThe solvent was removed under reduced pressure
4. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
5. washwashed with water (20 ml)
6. dry with materialdried over anhydrous magnesium sulphate
7. filtrationfiltered
8. customthe solvent removed under reduced pressure
9. customThe solid was purified by column chromatography on silica gel eluting with a gradient system of 97:3:0.3 (dichloromethane:methanol:ammonia)

ORD record

ord-80a0d2a19da54e699a0b78e020e89cab

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06897306B2