Ammonium Chloride → 5-(2-Amino-5-phenoxy-phenyl)-4-cyano-pentanoic acid cyclohexyl-methyl-amide

HRID 252464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252464
[CH:1]1([N:7]([CH3:32])[C:8](=[O:31])[CH2:9][CH2:10][CH:11]([C:29]#[N:30])[CH2:12][C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=[CH:15][C:14]=2[N+:26]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+]>[Zn].CO>[CH:1]1([N:7]([CH3:32])[C:8](=[O:31])[CH2:9][CH2:10][CH:11]([C:29]#[N:30])[CH2:12][C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:16]=[CH:15][C:14]=2[NH2:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 672695344-Cyano-5-(2-nitro-5-phenoxy-phenyl)-pentanoic acid cyclohexyl-methyl-amide

Produkt 1

HCID 672689265-(2-Amino-5-phenoxy-phenyl)-4-cyano-pentanoic acid cyclohexyl-methyl-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

4-cyano-5-(2-nitro-5-phenoxy-phenyl)-pentanoic acid cyclohexyl-methyl-amide (0.200 g, 0.46 mmol), ammonium chloride (0.31 g, 5.75 mmol) and methanol (3.0 mL) were added to a round bottom flask followed by addition of powdered zinc (0.4 g). The vessel was equipped with a condenser and the reaction was headed to reflux for 2 h followed by filtration through a pad of Celite®. The solvent was removed and the resulting residue was dissolved in ethyl acetate, then washed 3 times with 10% aqueous sodium carbonate solution. The organic layer was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The resulting residue was used in subsequent steps without further purification.

Aufarbeitung

  1. customThe vessel was equipped with a condenser
  2. temperatureto reflux for 2 h
  3. filtrationfollowed by filtration through a pad of Celite®
  4. customThe solvent was removed
  5. dissolutionthe resulting residue was dissolved in ethyl acetate
  6. washwashed 3 times with 10% aqueous sodium carbonate solution
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure
  10. customThe resulting residue was used in subsequent steps without further purification

Quellen und Nachweise

ORD-Eintrag
ord-2beef67311c742df8b3b5600af04c18d
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868022B2

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