Sodium Chloride → [(r)-2-(Tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester

HRID 20339

反応式

HRID 20339 の反応式
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C([O:23][CH2:24][CH3:25])=C.[I:26]N1C(=O)CCC1=O.[Cl-].[Na+].[C:36](#N)[CH3:37]>>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([CH:9]([O:23][CH2:24][CH2:25][I:26])[O:10][CH2:36][CH3:37])[CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 5

HCID 5234Sodium ChlorideHCID 6342AcetonitrileHCID 8023Ethyl vinyl etherHCID 120273N-IodosuccinimideHCID 10913779(R)-(+)-N-(tert-Butoxycarbonyl)-O-(tert-butyldimethylsilyl)serinol

生成物 1

HCID 86615364[(r)-2-(Tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester収率 34%

実験手順

Dissolve [(R)-1-(tert-butyl-dimethylsilanyloxymethyl)-2-hydroxyethyl]-carbamic acid tert-butyl ester (1.0 g, 3.27 mmol) and ethyl vinyl ether (0.20 g, 2.73 mmol) in acetonitrile (20 mL) and add N-iodosuccinimide (0.735 g, 3.27 mmol). Stir at room temperature 72 hours and pour into saturated aqueous sodium chloride. Extract with ethyl acetate, wash with water and saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify (silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate) to give the desired compound (462 mg, 34%).

後処理

  1. extractionExtract with ethyl acetate
  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 100:0 to 10:90 hexanes:ethyl acetate)

出典と根拠

ORDレコード
ord-86666333ce9343dcba6d302be914e1c2
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

関連ノート

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