Water → HCID 44512057, compound

HRID 2193862Notes

Reaction equation

HRID 2193862 reaction equation
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[CH:12]=1.[Cl-:18].O>ClCCl>[CH3:14][O:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:12]=[C:3]([C@H:2]([CH3:1])[C:15]([O:17][CH2:1][CH2:2][CH2:3][CH2:12][Cl:18])=[O:16])[CH:4]=[CH:5]2

Participants

4

Reactant 2

HCID 962WaterHCID 86584140(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid chloride

Product 1

HCID 44512057HCID 44512057, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Preparation: 30 g of Naproxen chloride are dissolved in 120 g of dichloromethane. This solution is cooled at 0° C. and a solution of 14.5 g of 1-chloro-3-buthanol in 100 g of dichloromethane is added dropwise in 2 hours. After a completion time of 3 hours at 0° C., 60 g of water are added and is the mixture is stirred for 10 hours. After phase separation, 60 g of water are added to organic phase and the mixture is stirred for 10 hours. After phase separation, the organic phase is concentrated to 120 mL and 4.5 g of potassium carbonate are added. The mixture is refluxed at about 40° C. for 4 hours. After filtration and vacuum concentration, an oil is obtained (HPLC purity 90%).

Workup

  1. customPreparation
  2. customAfter phase separation, 60 g of water
  3. additionare added to organic phase
  4. stirringthe mixture is stirred for 10 hours
  5. customAfter phase separation
  6. concentrationthe organic phase is concentrated to 120 mL and 4.5 g of potassium carbonate
  7. additionare added
  8. temperatureThe mixture is refluxed at about 40° C. for 4 hours
  9. filtrationAfter filtration and vacuum concentration
  10. customan oil is obtained (HPLC purity 90%)

Sources & evidence

ORD record
ord-b99215b89e3142c49c7c81df1457f4ee
Source dataset
uspto-grants-2012_12
Patent number
US08329937B2

Reaction notes

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