Imidazole → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-ylcarbamate

HRID 409758노트

반응식

HRID 409758 반응식
[OH:1][CH2:2][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][CH:5]=[CH2:6].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[Si:20]([O:1][CH2:2][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][CH:5]=[CH2:6])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 14153343Tert-butyl (s)-(1-hydroxypent-4-en-2-yl)carbamate

생성물 1

HCID 14153345(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-ylcarbamate수율 85.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-tert-butyl 1-hydroxypent-4-en-2-ylcarbamate (165 g, 0.82 mol) and imidazole (72.5 g, 1.07 mol) in DCM (3 L) was added TBS-Cl (135.4 g, 0.9 mol). The reaction was stirred at RT overnight and filtered. The filtrate was concentrates. The resulting residue was dissolved in EtOAc (L) and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-ylcarbamate (222.0 g), which was used in the next step without further purification. LRMS (M+H+) m/z 316.2.

후처리

  1. filtrationfiltered
  2. dissolutionThe resulting residue was dissolved in EtOAc (L)
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-33c168a47ef84677b88f987f560aebbb
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759374B2

반응 노트

불러오는 중…