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

HRID 20405

反応式

HRID 20405 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-bffe4dffcbdc41dca34b21a93476b393
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

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