تفاعل #161014

معادلة التفاعل

1-aminocyclohexanecarboxylic acid methyl ester

di-t-butyl dicarbonate

triethylamine

thiazolidine

→

title compound

المردود 66.9%

1-[(3-Thiazolidinylcarbonyl)amino]cyclohexanecarboxylic acid

المردود 66.9%

المذيبات

methylene chloride

methylene chloride

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   تركيزAfter the reaction solution was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   غسيلthe mixture was washed with water
5. 5
   تجفيفby drying with anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONAfter the solvent was distilled off under reduced pressure, tetrahydrofuran and 1N aqueous sodium hydroxide solution
7. 7
   workup.ADDITIONwere added to the residue
8. 8
   درجة الحرارةthe mixture was heated
9. 9
   درجة الحرارةunder reflux for 3 hours
10. 10
    workup.ADDITIONAfter ether was added to the reaction solution
11. 11
    غسيلto wash it
12. 12
    استخلاصwas extracted with ethyl acetate
13. 13
    غسيلAfter the obtained organic layer was washed with saturated brine, it
14. 14
    تجفيفwas dried with anhydrous sodium sulfate
15. 15
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure

الإجراء التجريبي

A solution of 78 mg (0.6 mmol) of N,N-dimethylaminopyridine and 1 g (6.36 mmol) of 1-aminocyclohexanecarboxylic acid methyl ester in methylene chloride was added to a solution of 1.39 mg (6.36 mmol) of di-t-butyl dicarbonate in 10 ml of methylene chloride, and the mixture was stirred at room temperature for 30 minutes. Thereafter, a solution of 1.29 g (12.7 mmol) of triethylamine and 680 mg (7.6 mmol) of thiazolidine in methylene chloride was added thereto, and the mixture was stirred at room temperature overnight. After the reaction solution was concentrated, the residue was dissolved in ethyl acetate, and the mixture was washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, tetrahydrofuran and 1N aqueous sodium hydroxide solution were added to the residue, and the mixture was heated under reflux for 3 hours. After ether was added to the reaction solution to wash it, the aqueous layer was neutralized by concentrated hydrochloric acid, 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 to obtain 1.1 g (66%) of the title compound.

المصدر