Lithium Hydroxide → (2S)-2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanol

HRID 1739432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739432
BrC1C=C(C=CN=1)C([O:7][CH2:8][C@@H:9]([NH:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([Br:29])[CH:24]=1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=O.[OH-].[Li+]>CO>[Br:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][N:26]=1)[C:22]([NH:21][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[CH2:8][OH:7])=[O:30]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 56981746(2S)-1-(2-bromoisonicotinoyloxy)-2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)propane

Produkt 1

HCID 57095136(2S)-2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanolAusbeute 37,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of (2S)-1-(2-bromoisonicotinoyloxy)-2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)propane (4.68 g) in methanol (100 ml) is added a 1 M lithium hydroxide (8.1 ml), and the mixture is stirred for 15 hours. The reaction mixture is concentrated under reduced pressure to remove the methanol, and the residue is extracted with methylene chloride. The extract is washed, dried, and concentrated. The residue is purified by silica gel chromatography (solvent; chloroform:acetone=5:1) to give (2S)-2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanol (1.2 g).

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto remove the methanol
  3. extractionthe residue is extracted with methylene chloride
  4. washThe extract is washed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel chromatography (solvent; chloroform:acetone=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-87180e24245c4dd68caee8f4e4c9e2ae
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965730

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