Triethylamine → (2S,3R)-N-cyclopropyl-3-propyl-2-oxiranecarboxamide

Temperature

-20 °C

(2S,3R)-3-Propyl-2-oxiranecarboxylic acid (118 mg, 0.8 mmol), triethylamine (0.8 mmol) and tetrahydrofuran (2 ml) were mixed, and the mixture was cooled to −20° C. A tetrahydrofuran solution (1 ml) of ethoxycarbonyl chloride (86 mg, 0.8 mmol) was gradually added, and the mixture was stirred at the same temperature for 30 minutes. A tetrahydrofuran solution (1 ml) of cyclopropylamine (48 mg, 0.8 mmol) was gradually added dropwise, and the mixture was stirred at the same temperature for 2 hours and at room temperature for 2 hours. After the reaction was quenched with water (10 ml), ethyl acetate (10 ml) was added and the solvent was evaporated away under reduced pressure. The mixture was extracted with ethyl acetate (10 ml), and washed with water (5 ml). The solvent was evaporated away under reduced pressure to obtain the title compound as a colorless oil (0.10 g, yield: 76%).

1. stirringthe mixture was stirred at the same temperature for 2 hours and at room temperature for 2 hours
2. customAfter the reaction was quenched with water (10 ml), ethyl acetate (10 ml)
3. additionwas added
4. customthe solvent was evaporated away under reduced pressure
5. extractionThe mixture was extracted with ethyl acetate (10 ml)
6. washwashed with water (5 ml)
7. customThe solvent was evaporated away under reduced pressure

ORD record

ord-626224b7b73f4b84b19d888ca068bd7c

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834190B2