4-(Bromomethyl)benzoic acid → N-{1-[(Cyano-dimethyl-methyl)-carbamoyl]-3-methyl-butyl)-4-bromomethyl-benzamide

HRID 276708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 276708
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.[C:22]([C:24]([NH:27][C:28](=[O:35])[CH:29]([NH2:34])[CH2:30][CH:31]([CH3:33])[CH3:32])([CH3:26])[CH3:25])#[N:23]>CN(C)C=O>[C:22]([C:24]([NH:27][C:28]([CH:29]([NH:34][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([CH2:2][Br:1])=[CH:11][CH:10]=1)[CH2:30][CH:31]([CH3:32])[CH3:33])=[O:35])([CH3:26])[CH3:25])#[N:23]

Komponenten

5

Edukt 3

HCID 225994-(Bromomethyl)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 539013662-Amino-4-methyl-pentanoic acid (cyano-dimethyl-methyl)-amide

Produkt 1

HCID 18316679N-{1-[(Cyano-dimethyl-methyl)-carbamoyl]-3-methyl-butyl)-4-bromomethyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

4-Bromomethylbenzoic acid (4.1 mmol), HOBt (4.1 mmol) and WSCD.HCI (4.1 mmol) are dissolved in dimethylformamide (7 ml) and stirred for 10 min. 2-Amino-4-methyl-pentanoic acid (cyano-dimethyl-methyl)-amide (4.1 mmol) is added in DMF (3 ml) and the reaction mixture is stirred at RT overnight. After evaporation of the solvent, the residue is extracted with ethyl acetate. The extract is washed with water, 10% citric acid, brine, sodium bicarbonate, brine and dried over magnesium sulfate and evaporated. The crude product is suspended in diethylether and the solid filtered of and dried (vacuum). A white powder with mp. 185-187° C., Rf=0.43 (n-hexane:ethyl acetate=1:1) is obtained.

Aufarbeitung

  1. stirringthe reaction mixture is stirred at RT overnight
  2. customAfter evaporation of the solvent
  3. extractionthe residue is extracted with ethyl acetate
  4. washThe extract is washed with water, 10% citric acid, brine, sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. filtrationthe solid filtered of and
  8. customdried (vacuum)
  9. customA white powder with mp. 185-187° C., Rf=0.43 (n-hexane:ethyl acetate=1:1) is obtained

Quellen und Nachweise

ORD-Eintrag
ord-3519902a1dbb48f2b0966711c6a79c4f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353017B1

Notizen zur Reaktion

Wird geladen…