Lithium Hydroxide → HCID 25123611, compound

HRID 1361099Notes

Reaction equation

HRID 1361099 reaction equation
[OH-].[Li+].[CH2:3]([S:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[C:22]([O:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:21]=2)=[CH:13][C:12]=1[O:37][CH3:38])(=[O:9])=[O:8])[CH2:4][CH2:5][CH3:6]>O1CCCC1>[CH2:3]([S:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[C:22]([O:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:21]=2)=[CH:13][C:12]=1[O:37][CH3:38])(=[O:8])=[O:9])[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86642718HCID 86642718, compound

Product 1

HCID 25123611HCID 25123611, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.66 ml (0.66 mmol) of aqueous 1M lithium hydroxide solution is added to a solution of 171 mg (0.33 mmol) of methyl 3-(4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-2-butoxyphenyl)propanoate in 3 ml of tetrahydrofuran, and the reaction mixture is then stirred for 18 hours at room temperature. After evaporating to dryness, the reaction medium is taken up in 10 ml of water and acidified with acetic acid to pH 4, and then extracted with ethyl acetate. The organic phases are combined, dried over sodium sulfate and filtered. The solvents are evaporated off and the residue is then purified by chromatography on a column of silica eluted with a 99/1 dichloromethane/methanol mixture. 99 mg (60%) of 3-(4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-2-butoxyphenyl)propanoic acid are obtained in the form of a yellow oil.

Workup

  1. customAfter evaporating to dryness
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvents are evaporated off
  6. customthe residue is then purified by chromatography on a column of silica
  7. washeluted with a 99/1 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-ae36ebfb97954b84aa156d3b9ec76bfb
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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