Ethyl Acetate → {(S)-2-benzyloxy-1-[1-(2,2-dimethylpropoxy)-2-iodoethoxymethyl]-ethyl}-carbamic acid tert-butyl ester

HRID 20405

반응식

HRID 20405 반응식
[I:1]N1C(=O)CCC1=O.[C:9]([O:13][C:14](=[O:28])[NH:15][C@H:16]([CH2:26][OH:27])[CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:12])([CH3:11])[CH3:10].[CH3:29][C:30]([CH3:36])([CH3:35])[CH2:31]OC=C.[C:37]([O:40]CC)(=O)[CH3:38]>C(#N)C>[C:9]([O:13][C:14](=[O:28])[NH:15][C@H:16]([CH:26]([O:40][CH2:37][CH2:38][I:1])[O:27][CH2:36][C:30]([CH3:29])([CH3:31])[CH3:35])[CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:12])([CH3:10])[CH3:11]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 120273N-IodosuccinimideHCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanolHCID 148973511-(Ethenyloxy)-2,2-dimethylpropane

생성물 1

HCID 68561131{(S)-2-benzyloxy-1-[1-(2,2-dimethylpropoxy)-2-iodoethoxymethyl]-ethyl}-carbamic acid tert-butyl ester수율 84.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

Add N-iodosuccinimide (14.19 g, 74.63 mmol) to ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (15.00 g, 53.30 mmol) and 2,2-dimethyl-1-vinyloxypropane (9.13 g, 79.96 mmol) in acetonitrile (267 mL) at room temperature. Heat to 60° C. under nitrogen for 2 hours. Cool to room temperature and dilute with ethyl acetate. Wash with water and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the desired compound as an oil (23.4 g 84.2%).

후처리

  1. temperatureCool to room temperature
  2. washWash with water and saturated aqueous sodium chloride
  3. dry with materialDry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-bffe4dffcbdc41dca34b21a93476b393
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

연결된 노트

불러오는 중…