반응 #46662

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.ADDITIONwater (27 ml) and tetrahydrofuran (30 ml) were added to the concentrate
5. 5
   workup.STIRRINGthe whole 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
   건조dried over sodium sulfate
9. 9
   농축concentrated under reduced pressure
10. 10
    기타The resulting residue was separated 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 to the reaction mixture, the whole was concentrated under reduced pressure, then water (27 ml) and tetrahydrofuran (30 ml) were added to the concentrate, and the whole was stirred at room temperature. A solution of di-t-butyl carbonate (9.43 g, 43.2 mmol) in tetrahydrofuran (6 ml) was added thereto, and after 15 minutes, citric acid monohydrate was added thereto to weakly acidify the whole. The whole was extracted with ethyl acetate (150 ml). The organic layer was washed with water (100 ml) and saturated brine (50 ml) successively, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was separated by silica gel column chromatography to give 2-[N-(t-butoxycarbonyl)-N-propylamino]acetic acid (5.06 g, 65%) as a colorless solid.

출처