Sodium Hydroxide → HCID 20636575, compound

HRID 49722Notes

Reaction equation

HRID 49722 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([CH:24]([CH3:31])[CH2:25][C:26]([O:28]CC)=[O:27])=[N:22][CH:23]=2)=[O:16])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])(=O)C.[OH-].[Na+]>CO.O>[OH:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([CH:24]([CH3:31])[CH2:25][C:26]([OH:28])=[O:27])=[N:22][CH:23]=2)=[O:16])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 17946656HCID 17946656, compound

Product 1

HCID 20636575HCID 20636575, compoundYield 40.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (RS) ethyl 3-{5-[2-(3-acetoxy-4-nitrophenyl)-acetylamino]-pyridin-2-yl}-butanoate (6.18 g, Reference Example 27) in methanol (100 mL) was treated with a solution of sodium hydroxide (3.5 g) in water (20 mL). The mixture was heated at 50° C. for 5 hours and then evaporated. The residue was dissolved in water and the resulting solution was washed with ethyl acetate, then acidified to pH 5 by addition of glacial acetic acid and then extracted with ethyl acetate. The extracts were washed with water, then dried over magnesium sulphate and then evaporated. The residual dark oil was subjected to flash chromatography on silica eluting with ethyl acetate to give the title compound (2.1 g) as a brown solid.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in water
  3. washthe resulting solution was washed with ethyl acetate
  4. additionacidified to pH 5 by addition of glacial acetic acid
  5. extractionextracted with ethyl acetate
  6. washThe extracts were washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-18d9095f6f974fe5832c3676a1755e72
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

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