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

HRID 1739432Notes

Reaction equation

HRID 1739432 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

HCID 57095136(2S)-2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanolYield 37.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-87180e24245c4dd68caee8f4e4c9e2ae
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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