반응 #87123

반응 방정식

N,O-dimethylhydroxylamine HCl

(S)-2-(tert-Butoxycarbonylamino)-3-cyclopentenylpropanoic acid

ethyl chloroformate

NMM

→

(S)-tert-butyl (3-(cyclopent-1-en-1-yl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate

수율 94.0%

용매

DCM

THF DCM

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   온도The mixture was cooled to 0° C.
3. 3
   온도to warm to ambient temperature
4. 4
   workup.STIRRINGstirred overnight
5. 5
   기타The mixture was quenched with water (500 mL)
6. 6
   세척the organic phase was washed with water (500 mL)
7. 7
   건조dried over anhydrous sodium sulfate
8. 8
   농축concentrated

실험 절차

To a flask charged with (S)-2-(tert-Butoxycarbonylamino)-3-cyclopentenylpropanoic acid (55.0 g, 214 mmol) was added THF/DCM (800 mL, 1:1). The solution was cooled to 0° C. and ethyl chloroformate (24.5 mL, 257 mmol) and NMM (28.4 mL, 257 mmol) were added dropwise sequentially. After addition, the mixture was stirred at 0° C. under nitrogen for 1 h. To the other flask charged with N,O-dimethylhydroxylamine HCl (25 g, 257 mmol) was added DCM (400 mL). The mixture was cooled to 0° C. and TEA (38.7 mL, 278 mmol) was added. The resulting mixture was transferred into the former reaction flask. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The mixture was quenched with water (500 mL) and the organic phase was washed with water (500 mL), dried over anhydrous sodium sulfate, and concentrated to afford (S)-tert-butyl (3-(cyclopent-1-en-1-yl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate as colorless oil (60 g, 93% yield), which was used in the next step without further purification.

출처