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

HRID 20339

Reaktionsgleichung

Reaktionsgleichung von HRID 20339
[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]

Komponenten

6

Edukt 5

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

Produkt 1

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

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-86666333ce9343dcba6d302be914e1c2
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745438B2

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