تفاعل #161022

معادلة التفاعل

1-aminocyclohexanecarboxylic acid

sodium hydrogencarbonate

5-methylisoxazole-4-carboxylic acid

thionyl chloride

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

title compound

المردود 16.0%

2-(5-Methylisoxazol-4-yl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

المردود 16.0%

المذيبات

toluene

water

ظروف التفاعل

المعالجة

1. 1
   تركيزUnder reduced pressure, the reaction solution was concentrated
2. 2
   workup.STIRRINGAfter the mixture was stirred at room temperature overnight
3. 3
   أخرىthe toluene layer was separated
4. 4
   استخلاصwas extracted with ethyl acetate
5. 5
   غسيلAfter the obtained organic layer was washed with saturated brine, it
6. 6
   تجفيفwas dried with anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure, methylene chloride
8. 8
   workup.ADDITIONwas added
9. 9
   درجة الحرارةunder ice-cooling
10. 10
    workup.STIRRINGAfter the mixture was stirred at room temperature overnight, under reduced pressure
11. 11
    تركيزthe reaction solution was concentrated
12. 12
    workup.ADDITIONethyl acetate was added
13. 13
    غسيلthe mixture was successively washed with water
14. 14
    تجفيفby drying with anhydrous sodium sulfate
15. 15
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure

الإجراء التجريبي

1 g (7.87 mmol) of 5-methylisoxazole-4-carboxylic acid was added to 3 ml of thionyl chloride, and the mixture was stirred overnight. Under reduced pressure, the reaction solution was concentrated, and the obtained residue was added to a solution of 1.13 g (7.87 mmol) of 1-aminocyclohexanecarboxylic acid and 6.6 g (79 mmol) of sodium hydrogencarbonate in 30 ml of toluene-30 ml of water. After the mixture was stirred at room temperature overnight, the toluene layer was separated. The aqueous layer was neutralized by potassium hydrogensulfate, and it was extracted with ethyl acetate. After the obtained organic layer was washed with saturated brine, it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, methylene chloride was added thereto, and under ice-cooling, 332 mg (1.73 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added. After the mixture was stirred at room temperature overnight, under reduced pressure, the reaction solution was concentrated, ethyl acetate was added thereto, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 295 mg (16%) of the title compound.

المصدر