Water → tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-(tert-butyldimethylsilyloxy) butyl)cyclopropanecarboxylate

HRID 1967286노트

반응식

HRID 1967286 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:25][CH3:26])[CH:13]([C:15]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]1)[OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O)(=O)=O.[C:43]([SiH:47]([CH3:49])[CH3:48])([CH3:46])([CH3:45])[CH3:44].O>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:25][CH3:26])[CH:13]([C:15]1([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:17][CH2:16]1)[O:14][Si:47]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:49])[CH3:48])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 79372,6-LutidineHCID 67104998tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-hydroxybutyl)cyclopropanecarboxylateHCID 131728534Tert-butyldimethylsilane trifluoromethanesulfonate

생성물 1

HCID 59556935tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-(tert-butyldimethylsilyloxy) butyl)cyclopropanecarboxylate수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-hydroxybutyl)cyclopropanecarboxylate (914.8 mg) and 2,6-lutidine (0.632 mL) in tetrahydrofuran (20 mL) was added under ice-cooling tert-butyldimethylsilane trifluoromethanesulfonate (0.934 mL) and, after warming to room temperature, the mixture was stirred for 1 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→2/1) to give the title compound as a colorless oil (yield: 1.18 g, 98%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→2/1)

출처 및 근거

ORD 기록
ord-f5a12b8ddb864fdf9013e6b692045bab
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420694B2

반응 노트

불러오는 중…