Methanesulfonyl chloride → N-Benzyl-N-[2-(methanesulphonyloxy)ethyl]-glycine tert-butyl ester

HRID 54613

Reaktionsgleichung

Reaktionsgleichung von HRID 54613
[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1.ClCCl>[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH2:10][O:11][S:21]([CH3:20])(=[O:23])=[O:22])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 15817339Tert-butyl 2-(benzyl (2-hydroxyethyl)amino)acetate

Produkt 1

HCID 15817340N-Benzyl-N-[2-(methanesulphonyloxy)ethyl]-glycine tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product from Example 1 (10.0 g; 38 mmol) is dissolved in anhydrous pyridine (185 ml), and methanesulphonyl chloride (3.7 ml; 46 mmol) is slowly added dropwise at 0° C. The solution is stirred at room temperature for 6.5 h. Subsequently, the solution is diluted with dichloromethane (740 ml) and extracted twice with a 10% solution of sodium hydrogen carbonate (250 ml on each occasion). The organic phase is dried (magnesium sulphate) and concentrated, and the residue is subsequently distilled repeatedly with toluene. Yield: 10.79 g (85%), brown oil.

Aufarbeitung

  1. extractionextracted twice with a 10% solution of sodium hydrogen carbonate (250 ml on each occasion)
  2. dry with materialThe organic phase is dried (magnesium sulphate)
  3. concentrationconcentrated
  4. distillationthe residue is subsequently distilled repeatedly with toluene

Quellen und Nachweise

ORD-Eintrag
ord-39c4d32e1cfd4a67a3068266aedf474b
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623049

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