Triethylamine → (R)-1-(1-phenylethyl)urea

To (1R)-1-phenylethylamine (1 g) and triethylamine (1.15 ml) in tetrahydrofuran (25 ml) solution, 4-nitrophenylchlorocarbonate (1.66 g) was added at −20° C. and the mixture was stirred at room temperature for 30 minutes. Further, 28% ammonia water (4 ml) was added to the reaction solution and the mixture was stirred at room temperature for 30 minutes. The tetrahydrofuran was distilled off in vacuo, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with 2N sodium hydroxide aqueous solution, distilled water, saturated potassium hydrogensulfate aqueous solution, and saturated saline and dried over with anhydrous sodium sulfate, then concentrated. The residue was recrystallized from ethyl acetate/hexane to obtain the title compound (860 mg).

1. stirringthe mixture was stirred at room temperature for 30 minutes
2. distillationThe tetrahydrofuran was distilled off in vacuo
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was successively washed with 2N sodium hydroxide aqueous solution
5. distillationdistilled water, saturated potassium hydrogensulfate aqueous solution, and saturated saline
6. dry with materialdried over with anhydrous sodium sulfate
7. concentrationconcentrated
8. customThe residue was recrystallized from ethyl acetate/hexane

ORD record

ord-a9ed3043003a43cd9e1ba5e89f2dff19

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888348B2