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

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, 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 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.

1. stirringthe mixture was stirred at room temperature overnight
2. concentrationAfter the reaction solution was concentrated
3. dissolutionthe residue was dissolved in ethyl acetate
4. washthe mixture was washed with water
5. dry with materialby drying with anhydrous sodium sulfate
6. distillationAfter the solvent was distilled off under reduced pressure, tetrahydrofuran and 1N aqueous sodium hydroxide solution
7. additionwere added to the residue
8. temperaturethe mixture was heated
9. temperatureunder reflux for 3 hours
10. additionAfter ether was added to the reaction solution
11. washto wash it
12. extractionextracted with ethyl acetate
13. washAfter the obtained organic layer was washed with saturated brine, it
14. dry with materialwas dried with anhydrous sodium sulfate
15. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-1ba1fe90b8124380b34e10dba1823c64

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785631B2