Potassium Carbonate → ethyl (S)-2-ethoxy-3-[4-[[4-(methylsulfonyloxy)phenethyl]oxy]phenyl]propanoate

HRID 1384424Notes

Reaction equation

HRID 1384424 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13]CS([O-])(=O)=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH2:19]([O:21][C:22](=[O:35])[C@@H:23]([O:32][CH2:33][CH3:34])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[CH3:20].C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=O.[Mg+2]>C(#N)C>[CH2:19]([O:21][C:22](=[O:35])[C@@H:23]([O:32][CH2:33][CH3:34])[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH2:13][CH2:12][C:9]2[CH:8]=[CH:7][C:6]([O:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][CH:10]=2)=[CH:29][CH:30]=1)[CH3:20]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 227084532-(4-Methylsulfonyloxyphenyl)ethylmethanesulfonate2×

Product 1

HCID 11293498ethyl (S)-2-ethoxy-3-[4-[[4-(methylsulfonyloxy)phenethyl]oxy]phenyl]propanoateYield 151%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-(4-methanesulfonyloxyphenyl)ethylmethanesulfonate (described in Example 1a) (2.41 g; 8.14 mmole) in acetonitrile (11.8 ml) was added to a mixture of (S)-2-ethoxy-3-(4-hydroxyphenyl) propanoic acid ethyl ester (1.3 g; 5.46 mmole), potassium carbonate (2.26 g; 16.4 mmole) and magnesium sulfate (1 g) in acetonitrile (50 ml). The reaction mixture was refluxed for 19 hours. More of 2-(4-methanesulfonyloxyphenyl)ethyl-methanesulfonate (0.8 g; 2.73 mmole) was added and the reaction mixture was refluxed for another 25 hours. Solid material was filtered off and the solvent was evaporated in vacuo to give 3.6 g of (S)-2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]-propanoic acid ethyl ester.

Workup

  1. temperatureThe reaction mixture was refluxed for 19 hours
  2. temperaturethe reaction mixture was refluxed for another 25 hours
  3. filtrationSolid material was filtered off
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fd056f4313b7432da707512a0ae982c4
Source dataset
uspto-grants-2001_07
Patent number
US06258850B1

Reaction notes

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