Triethylamine → HCID 68996327, 화합물

To an ice-cold solution of 1-methylcyclopropanecarboxylic acid (214 mg, 2.14 mmol) in dichloromethane (10 mL) was added oxalyl chloride (0.19 mL, 2.14 mmol) dropwise. The ice bath was removed and stirring was continued for 1 h. 2-Amino-3-hydroxybenzoic acid hydrobromide (500 mg, 2.14 mmol) was added followed by triethylamine (0.90 mL, 6.42 mmol). The resulting reaction mixture was stirred at room temperature overnight. The reaction was quenched with aqueous 1 N HCl (25 mL) until the solution reached pH 1. The reaction mixture was extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and concentrated to a brown solid. The crude was dissolved in toluene (10 mL) and the solution was treated with p-toluenesulfonic acid monohydrate (477 mg, 2.50 mmol). The reaction mixture was then heated to reflux for 1 h. The reaction was cooled to room temperature, poured into water and extracted with ethyl acetate. The organic layer was separated, then washed with water (5×50 mL), brine, dried (Na2SO4), filtered and concentrated to afford 2-(1-methylcyclopropyl)benzoxazole-4-carboxylic acid (306 mg, 65%) as a light yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 12.89 (br s, 1H), 7.85 (dd, J=8.0, 0.9 Hz, 1H), 7.81 (dd, J=7.7, 0.9 Hz, 1H), 7.39 (t, J=7.9 Hz, 1H), 2.91 (s, 3H), 1.42-1.37 (m, 2H), 1.10-1.05 (m, 2H); MS (ESI+) m/z 218 (M+H).

1. customThe ice bath was removed
2. customThe resulting reaction mixture
3. stirringwas stirred at room temperature overnight
4. customThe reaction was quenched with aqueous 1 N HCl (25 mL) until the solution
5. extractionThe reaction mixture was extracted with dichloromethane
6. dry with materialThe combined organic layers were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated to a brown solid
9. dissolutionThe crude was dissolved in toluene (10 mL)
10. temperatureThe reaction mixture was then heated
11. temperatureto reflux for 1 h
12. extractionextracted with ethyl acetate
13. customThe organic layer was separated
14. washwashed with water (5×50 mL), brine
15. dry with materialdried (Na2SO4)
16. filtrationfiltered
17. concentrationconcentrated

ORD 기록

ord-3cff13e0899644c297d32fefdf0e6485

출처 데이터셋

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07553846B2