Methyl iodide → 2-[(4-Methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-3-methoxymethyl-benzoic acid methyl ester

HRID 583393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583393
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][OH:11])[C:5]=1[N:12]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[H-].[Na+].I[CH3:35]>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][CH3:35])[C:5]=1[N:12]([S:20]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)(=[O:22])=[O:21])[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 701992853-Hydroxymethyl-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-benzoic acid methyl ester

Produkt 1

HCID 538692052-[(4-Methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-3-methoxymethyl-benzoic acid methyl esterAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.200 g (0.452 mmol) of the product of Example 336 in 5.0 mL of dry THF was added 0.022 g (0.543 mmol) of 60% sodium hydride followed by 0.028 mL of iodomethane. The reaction was stired at room temperature for 18 h and then diluted with ethyl acetate. The organics were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with EtOAc to provide 0.057 g (28%) of the methyl ether as ayellow solid. Electrospray Mass Spec: 457.3 (M+H)+.

Aufarbeitung

  1. washThe organics were washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-a21cafe8f45d43bbb32ecf2470cbf6ac
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929097

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