Ethyl Acetate → HCID 66879199, 화합물

To a 100 mL round-bottom vessel was charged 2-(4-(ethoxycarbonyl)cyclohexyl)acetic acid (Int-4c, 4.03 g, 18.79 mmol) and THF (20 mL). To this solution was added N,N′-carbonyldiimidazole (3.66 g, 22.55 mmol). The resulting solution was allowed to stir 18 hours at room temperature. After 18 hours, in a separate 250 mL round-bottom vessel, 80 mL THF was added and the flask was flushed with argon. This solution was cooled to −78° C. in dry ice/IPA bath. To this solution was added LiHMDS (1.0 M in THF, 39.46 mmol, 39.46 mL). To the resulting solution was added dropwise dry EtOAc (40.4 mmol, 3.95 mL). This solution was allowed to stir at −78° C. for one hour. After one hour, the solution of crude ethyl 4-(2-(1H-imidazol-1-yl)-2-oxoethyl)cyclohexanecarboxylate (Int-4d) in THF was added dropwise. This solution was allowed to gradually warm to room temperature and the reaction was stirred overnight. After 18 hours, the reaction was quenched with saturated NH4Cl(aq) and extracted with Et2O (x3). The combined organics were dried over Na2SO4 and the residue was purified via silica gel chromatography to yield the title compound as clear oil. Yield=2.33 g.

1. waitAfter 18 hours
2. customthe flask was flushed with argon
3. temperatureThis solution was cooled to −78° C. in dry ice/IPA bath
4. stirringto stir at −78° C. for one hour
5. waitAfter one hour
6. temperatureto gradually warm to room temperature
7. stirringthe reaction was stirred overnight
8. waitAfter 18 hours
9. customthe reaction was quenched with saturated NH4Cl(aq)
10. extractionextracted with Et2O (x3)
11. dry with materialThe combined organics were dried over Na2SO4
12. customthe residue was purified via silica gel chromatography

ORD 기록

ord-60a37e04966a471db408396bfd7255bb

출처 데이터셋

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08609675B2