반응 #51516

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N-(t-butoxycarbonyl)-N-benzyl-L-phenylalaninol

N-(t-Butoxycarbonyl)-N-benzyl-L-phenylalaninol

triethylamine

Water

→

N-(t-Butoxycarbonyl)-N-benzyl-L-phenylalaninal

수율 100.0%

용매

dimethyl sulfoxide

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후처리

1. 1
   추출the mixture was extracted with 20 mL of ethyl acetate
2. 2
   세척The organic layer was washed with 20 mL of 5% citric acid, 20 mL of water, 20 mL of brine
3. 3
   건조dried over magnesium sulfate
4. 4
   여과filtered
5. 5
   농축The filtrate was concentrated under reduced pressure

실험 절차

To a solution of 2.38 g (6.98 mmoles) of N-(t-butoxycarbonyl)-N-benzyl-L-phenylalaninol from Example 17 in 3.8 mL (27.2 mmoles) of triethylamine at 10° C. was added a solution of 4.33 g (27.2 mmoles) of sulfur trioxide pyridine complex in 17 mL of dimethyl sulfoxide. The mixture was warmed to room temperature and stirred for one hour. Water (16 mL) was added and the mixture was extracted with 20 mL of ethyl acetate. The organic layer was washed with 20 mL of 5% citric acid, 20 mL of water, 20 mL of brine, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 2.37 g (100% yield) of N-(t-Butoxycarbonyl)-N-benzyl-L-phenylalaninal.

출처