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Methyl iodide → [4-(Tert-butyl-dimethyl-silanyloxy)phenyl]-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-acetic acid methyl ester

HRID 2084895
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2084895
[CH3:1][O:2][C:3](=[O:34])[CH:4]([C:20]1[CH:25]=[CH:24][C:23]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[CH:22][CH:21]=1)[NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]#[C:18][CH3:19])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[H-].[Na+].I[CH3:38]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:34])[CH:4]([C:20]1[CH:21]=[CH:22][C:23]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:28])[CH3:29])=[CH:24][CH:25]=1)[N:5]([S:6]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]#[C:18][CH3:19])=[CH:13][CH:14]=1)(=[O:8])=[O:7])[CH3:38]
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Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53702579[4-(Tert-butyl-dimethyl-silanyloxy) phenyl](4-but-2-ynyloxy-benzenesulfonylamino)-acetic acid methyl ester

Produkt 1

HCID 53639454[4-(Tert-butyl-dimethyl-silanyloxy)phenyl]-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 7.06 g (0.014 mmol) of [4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-(4-but-2-ynyloxy-benzenesulfonylamino)-acetic acid methyl ester dissolved in 50 mL of DMF was added 0.618 g (0.015 mmol) of a 60% oil dispersion of sodium hydride. The reaction was stirred for 30 min at room temperature and then 2.62 mL of iodomethane was added. After 5 h the reaction was diluted with water and extracted with ether. The combined organics were washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to provide [4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-acetic acid methyl ester as a white waxy solid. Electrospray Mass Spec 518.4 (M+H)+.

Aufarbeitung

  1. extractionextracted with ether
  2. washThe combined organics were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-3a870c29c6ac4d5596937ddbb4b6b24d
Quelldatensatz
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06716833B2

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