1-Bromo-4-fluorobutane → HCID 67436058, Verbindung

HRID 1662981

Reaktionsgleichung

Reaktionsgleichung von HRID 1662981
[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][CH2:34][CH2:35][CH2:36][F:37]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]([S:15]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:33][CH2:34][CH2:35][CH2:36][F:37])=[CH:22][CH:23]=1)(=[O:17])=[O:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1

Komponenten

6

Edukt 3

HCID 100221-Bromo-4-fluorobutaneHCID 11430Potassium CarbonateHCID 67435286[(4-Hydroxy-benzenesulfonyl)-(4-methoxy-benzyl)amino]-acetic acid methyl ester

Produkt 1

HCID 67436058HCID 67436058, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 1 g (2.74 mmol) of [(4-hydroxy-benzenesulfonyl)-(4-methoxy-benzyl)amino]-acetic acid methyl ester and 1.14 g (8.22 mmol) of K2CO3 in 8 ml of DMF, 0.59 ml (5.47 mmol) of 1-bromo-4-fluorobutane is added dropwise at r.t. After stirring for 18 h at r.t., the reaction mixture is diluted with H2O and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (AcOEt:n-hexane=3:1) to give {[4-(4-fluorobutoxy)-benzenesulfonyl](4-methoxy-benzyl)-amino}-acetic acid methyl ester; NMR (CDCl3): 1.86-1.96 (m, 4H), 3.57 (s, 3H), 3.79 (s, 3H), 3.90 (s, 2H), 4.08 (t, 2H, J=6.04 Hz), 4.39 (s, 2H), 4.46 (t, 1H, J=6.04 Hz), 4.55-4.65 (m, 1H), 6.83 (d, 2H, J=8.56 Hz), 6.97 (d, 2H, J=9.08 Hz), 7.15 (d, 2H, J=8.56 Hz), 7.82 (d, 2H, J=9.08 Hz).

Aufarbeitung

  1. additionis added dropwise at r.t
  2. extractionextracted with AcOEt
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel (AcOEt:n-hexane=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-e6d73a7fc56441cc9623d82a9fb4a2c7
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08034810B2

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