Ethanol → HCID 117840918, compound

Temperature

40 °C

In a 100 ml three-mouthed flask were charged crude (1S,2R)-ethyl 2-{4-(difluoromethoxy)benzoyl}aminocyclohexane-1-carboxylate (14 g, 41.0 mmol), and ethanol (42 ml), and the mixture was heated to 40° C. 5N Aqueous sodium hydroxide solution (9 ml, 45 mmol) was added, and the mixture was stirred at 40° C. for 2 hr 30 min. After cooling to 25° C., water (89 ml), toluene (28 ml) and heptane (28 ml) were added. The mixture was stirred and the aqueous layer was obtained. The aqueous layer was washed with a mixture of toluene (28 ml) and heptane (28 ml). To the aqueous layer was added acetonitrile (14 ml), and 6N hydrochloric acid and water (47 ml) were added to give crystals. The resulting crystals were collected by filtration, washed with water (70 ml) and then dried to give the title compound as a crude product. Recrystallization from an acetonitrile (80 ml)-water (120 ml) system gave the title compound as pale-gray crystals. yield 8.3 g. (diastereomeric excess>99.9% de) (enantiomeric excess>99.9% ee)

1. temperatureAfter cooling to 25° C.
2. stirringThe mixture was stirred
3. customthe aqueous layer was obtained
4. washThe aqueous layer was washed with a mixture of toluene (28 ml) and heptane (28 ml)
5. additionTo the aqueous layer was added acetonitrile (14 ml), and 6N hydrochloric acid and water (47 ml)
6. additionwere added
7. customto give crystals
8. filtrationThe resulting crystals were collected by filtration
9. washwashed with water (70 ml)
10. customdried

ORD record

ord-6e695037971141718686aabfd6092bc3

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238667B2