4-Phenoxybenzoic acid → HCID 68523477, 화합물

To a solution of 4-phenoxybenzoic acid (0.12 g, 0.55 mmol) in acetonitrile (5 ml) were added successively 1-hydroxybenzotriazole (88 mg, 0.65 mmol) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.12 g, 0.60 mmol), 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-N′-hydroxythiophene-2-carboximidamide (0.14 g, 0.5 mmol) that was obtained in Example 4 (4b) with stirring, and the resulting mixture was stirred at room temperature for 30 minutes. After stirring, water (5 ml) was added to the reaction mixture to quench the reaction, and the resulting mixture was extracted with ethyl acetate. The extract was washed successively with 0.1N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and dried over sodium sulfate. After filtration, the filtrate was evaporated in vacuo. Subsequently, to a solution of the residue obtained in tetrahydrofuran (4.0 ml) was added tetrabutylammonium fluoride (a 1.0 M solution in tetrahydrofuran, 1.0 ml, 11.0 mmol) with stirring, and the resulting mixture was stirred at 60° C. for 3 hours. After stirring, the reaction mixture was poured into water (20 ml) to quench the reaction and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over sodium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1) as the eluent to afford the title compound (97 mg) in a yield of 55% as a white crystalline solid.

1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
2. stirringAfter stirring
3. customto quench
4. customthe reaction
5. extractionthe resulting mixture was extracted with ethyl acetate
6. washThe extract was washed successively with 0.1N hydrochloric acid
7. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and dried over sodium sulfate
8. filtrationAfter filtration
9. customthe filtrate was evaporated in vacuo
10. customSubsequently, to a solution of the residue obtained in tetrahydrofuran (4.0 ml)
11. stirringwith stirring
12. stirringthe resulting mixture was stirred at 60° C. for 3 hours
13. stirringAfter stirring
14. customto quench
15. customthe reaction
16. extractionextracted with ether
17. washThe extract was washed with a saturated aqueous solution of sodium chloride
18. dry with materialdried over sodium sulfate
19. filtrationAfter filtration
20. customthe filtrate was evaporated in vacuo

ORD 기록

ord-b7707c93665b49648975059bcc4fe6d9

출처 데이터셋

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07687491B2