تفاعل #2054474

معادلة التفاعل

Water

ethyl (4S)-4-{[(benzyloxy)carbonyl]amino}-3-hydroxyhexanoate

2,6-lutidine

tert-butyldimethylsilane trifluoromethanesulfonate

→

ethyl (4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate

المردود 74.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   استخلاصthe mixture was extracted with ethyl acetate
3. 3
   تجفيفThe extract was dried over anhydrous magnesium sulfate
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   أخرىThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate-1/0→1/1)

الإجراء التجريبي

To a solution of ethyl (4S)-4-{[(benzyloxy)carbonyl]amino}-3-hydroxyhexanoate (63.2 g) and 2,6-lutidine (47.6 mL) in tetrahydrofuran (800 mL) was added tert-butyldimethylsilane trifluoromethanesulfonate (70 mL) under ice-cooling and, after warming to room temperature, and the mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate-1/0→1/1) to give ethyl (4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate as a colorless oil (yield: 64.0 g, 74%).

المصدر