Trifluoroacetic acid → (1S)-1-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]ethan-1-amine

2,2,2-Trifluoroacetic acid (4 mL, 52 mmol) was added to a solution of (S)-tert-butyl 1-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethylcarbamate (0.613 g, 1.89 mmol) in DCM (10 mL) at room temperature. The solution was stirred at room temperature for 1 hour and then concentrated in vacuo. The residue was dissolved in chloroform (100 mL) and washed with saturated aqueous sodium bicarbonate (100 mL). The layers were separated and the aqueous layer was extracted with chloroform (3×30 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give (S)-1-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethanamine (500 mg, yellow oil). The material was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.04 (d, J=8.7 Hz, 2H), 7.47 (d, J=8.6 Hz, 2H), 4.37 (q, J=6.9 Hz, 1H), 1.62 (d, J=6.9 Hz, 3H). MS m/z 224.0 (M+H)+; Rt-0.56 min.

1. concentrationconcentrated in vacuo
2. dissolutionThe residue was dissolved in chloroform (100 mL)
3. washwashed with saturated aqueous sodium bicarbonate (100 mL)
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with chloroform (3×30 mL)
6. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-063b41892a8441e592a5536359e05a67

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434719B2