반응 #11537

반응 방정식

bromoacetic acid

Propylamine

di-t-butyl carbonate

citric acid monohydrate

sodium hydroxide

→

2-[N-(t-butoxycarbonyl)-N-propylamino]acetic acid

수율 65.0%

용매

Ethanol

tetrahydrofuran

반응 조건

후처리

1. 1
   온도cooling
2. 2
   workup.STIRRINGthe whole was stirred at an external temperature of 80° C. for 2.5 hours
3. 3
   농축the whole was concentrated under reduced pressure
4. 4
   workup.ADDITIONThen, water (27 ml) and tetrahydrofuran (30 ml) were added to the concentrate
5. 5
   workup.STIRRINGthe mixture was stirred at room temperature
6. 6
   추출The whole was extracted with ethyl acetate (150 ml)
7. 7
   세척the organic layer was washed with water (100 ml) and saturated brine (50 ml) successively
8. 8
   건조The organic layer was dried over sodium sulfate
9. 9
   농축concentrated under reduced pressure
10. 10
    기타The residue was purified by silica gel column chromatography

실험 절차

Ethanol (36 ml) was added to bromoacetic acid (5.00 g, 36.0 mmol), and the mixture was stirred under ice-cold water-cooling. Propylamine (14.8 ml, 180 mmol) was added to the mixture over one minute, and then the whole was stirred at an external temperature of 80° C. for 2.5 hours. A 4 N aqueous sodium hydroxide solution (27 ml) was added thereto, and the whole was concentrated under reduced pressure. Then, water (27 ml) and tetrahydrofuran (30 ml) were added to the concentrate, and the mixture was stirred at room temperature. A solution of di-t-butyl carbonate (9.43 g, 43.2 mmol) in tetrahydrofuran (6 ml) was added to the mixture, and after 15 minutes, citric acid monohydrate was added to the reaction mixture to acidify it weakly. The whole was extracted with ethyl acetate (150 ml), and the organic layer was washed with water (100 ml) and saturated brine (50 ml) successively. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 5.06 g (65%) of 2-[N-(t-butoxycarbonyl)-N-propylamino]acetic acid as a colorless solid.

출처