Hydrochloric Acid → HCID 10132758, compound

A solution of (3R)-6-cyclohexyl-3-[3-(ethoxycarbonyl)-1,2,4-oxadiazol-5-yl]hexanoic acid (Preparation 4) (140 mg, 0.41 mmol) and N,N-diisopropylethylamine (320 μl, 2.07 mmol) in N,N-dimethylformamide (5 ml) was treated with O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (235 mg, 0.61 mmol) and the resulting solution was stirred at room temperature under a nitrogen atmosphere for 30 minutes. Hydroxylamine hydrochloride (113 mg, 0.61 mmol) was then added and the mixture was stirred at room temperature for 20 hours. The mixture was poured into hydrochloric acid (1M, 20 ml) and extracted with ethyl acetate (×3). The combined organic layers were washed sequentially with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (99.5:0.5) gradually changing to dichloromethane:methanol (97:3) to afford the title compound as a yellow oil (62 mg).

1. stirringthe mixture was stirred at room temperature for 20 hours
2. extractionextracted with ethyl acetate (×3)
3. washThe combined organic layers were washed sequentially with a saturated aqueous solution of sodium hydrogen carbonate and brine
4. dry with materialdried over anhydrous sodium sulphate
5. filtrationfiltered
6. customthe solvent removed under reduced pressure
7. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (99.5:0.5)

ORD record

ord-ee59f0fbdc5c4b4fb6bcbd68b57477f5

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06897306B2