Benzyl Bromide → {5-[Benzyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

HRID 15530

Reaktionsgleichung

Reaktionsgleichung von HRID 15530
[C:1]([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:28][CH2:29][CH3:30])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C)C=O>[C:1]([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:17]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[S:18]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)(=[O:19])=[O:20])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:28][CH2:29][CH3:30])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67201670[5-(4-Fluoro-benzenesulfonylamino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Produkt 1

HCID 67201023{5-[Benzyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The product from example 1, step d.) (1.13 g, 2.53 mmol) was dissolved in dimethylformamide (DMF) (30 mL), treated with K2CO3 (524 mg, 3.79 mmol), benzyl bromide (340 uL, 2.78 mmol), and stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed several times with water and concentrated under reduced pressure. This compound was purified by chromatography (EtOAc/Hex) prior to use in subsequent steps.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed several times with water
  3. concentrationconcentrated under reduced pressure
  4. customThis compound was purified by chromatography (EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-bb87bc151258406ca3087f33d7a83fd8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732618B2

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