Water → HCID 18182342, compound

HRID 1359384Notes

Reaction equation

HRID 1359384 reaction equation
[CH2:1]([C:8]1[C:13]([Br:14])=[CH:12][CH:11]=[C:10]([O:15][CH2:16][CH2:17][CH2:18][OH:19])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:27][O:28][C:29]([CH2:31][CH2:32][C:33](Cl)=[O:34])=[O:30].O>ClCCl>[CH2:1]([C:8]1[C:13]([Br:14])=[CH:12][CH:11]=[C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:33](=[O:34])[CH2:32][CH2:31][C:29]([O:28][CH3:27])=[O:30])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 18182283HCID 18182283, compound

Product 1

HCID 18182342HCID 18182342, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

509 mg of 2-benzyl-3-bromo-6-(3-hydroxypropyl)oxypyridine (Example 165a) was dissolved in 5 ml of dichloromethane. While stirring under ice-cooling, 0.33 ml of triethylamine and 0.29 ml of 3-methoxycarbonylpropionyl chloride were added thereto. After the temperature of the reaction solution was returned to room temperature and the reaction solution was stirred for 30 minutes, water was added to the reaction solution. The mixture was extracted with ethyl acetate, and the organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 20% ethyl acetate/hexane as an eluent for separation and purification, to give 643 mg of the target compound.

Workup

  1. temperaturecooling
  2. customwas returned to room temperature
  3. stirringthe reaction solution was stirred for 30 minutes
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic phase was further washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed
  8. customfor separation and purification

Sources & evidence

ORD record
ord-aa8cb1ca1dcb46009cbf4e01954e5200
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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