3-Pyridinecarboxaldehyde → 4-(3-Aminomethylpyridyl)-2-phenylbenzoylmethionine methyl ester

HRID 383093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383093
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[CH3:9][O:10][C:11](=[O:33])[C@H:12]([CH2:29][CH2:30][S:31][CH3:32])[NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18](N)=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH3-]C#[N:36].[Na+].C([O-])(O)=O.[Na+]>CO.C(O)(=O)C>[CH3:9][O:10][C:11](=[O:33])[C@H:12]([CH2:29][CH2:30][S:31][CH3:32])[NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18]([C:2]2[C:3]([CH2:7][NH2:36])=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 103713-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 18666758N-(4-Amino-2-phenylbenzoyl)methionine methyl ester

Produkt 1

HCID 206227934-(3-Aminomethylpyridyl)-2-phenylbenzoylmethionine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10129899Acetic acid methanolLösungsmittel

Versuchsvorschrift

A mixture of 3-pyridinecarboxaldehyde (1.0 equivalent), 4-amino-2-phenylbenzoyl methionine methyl ester (1.0 equivalent) and NaCNBH3 (1.0 equivalent) in methanol/acetic acid is stirred until the reaction is judged complete by TLC analysis. The mixture is poured into aqueous NaHCO3 and extracted into ethyl acetate which is dried and evaporated. Chromatography of the residue on silica gel affords the title compound.

Aufarbeitung

  1. extractionextracted into ethyl acetate which
  2. customis dried
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-417ca58903f2432982adf54519858250
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310095B1

Notizen zur Reaktion

Wird geladen…