Water → HCID 70055700, Verbindung

HRID 583320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583320
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[H-].[Na+].[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Cl.O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[N:12]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:32][C:31]1[CH:34]=[CH:35][CH:36]=[C:29]([O:28][CH3:27])[CH:30]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699943-Methoxybenzyl chlorideHCID 53963569HCID 53963569, Verbindung

Produkt 1

HCID 70055700HCID 70055700, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 0.699 g (2.0 mmol) of the product of Example 62 in 5 mL of DMF was added 0.096 g (2.4 mmol) of 60% sodium hydride. The resulting mixture was stirred for 30 min at room temperature and then 0.376 g (2.4 mmol) of m-methoxybenzyl chloride and 0.089 g (0.24 mmol) of tetrabutylammonium iodide were added. The reaction mixure was stirred for 18 hr at room temperature, poured into water and then extracted with ether. The combined organics were washed with water and brine, dried over MgSO4, filtered and concentad in vacuo. The crude solid was triturated with hexane to provide 0.768 g (82%) of the desired product as white solid. Electrospray Mass Spec 470.3 (M+H).

Aufarbeitung

  1. stirringThe reaction mixure was stirred for 18 hr at room temperature
  2. extractionextracted with ether
  3. washThe combined organics were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe crude solid was triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-3f7410b6ece84b2c9da6fc2068772de3
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929097

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