Acetic Acid → HCID 25128239, compound

HRID 1361078Notes

Reaction equation

HRID 1361078 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[CH:9]=[CH:10][C:11]=1[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[C:17]([O:26][CH3:27])[CH:16]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Li+].O.C(O)(=O)C>O1CCCC1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:9]=[CH:10][C:11]=1[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][S:22]([CH3:25])(=[O:23])=[O:24])=[C:17]([O:26][CH3:27])[CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 86761270HCID 86761270, compound

Product 1

HCID 25128239HCID 25128239, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

600 mg (1.25 mmol) of methyl 3-{3-butoxy-4-[3-(4-methanesulfonyloxy-3-methoxyphenyl)propyl]phenyl}propanoate are dissolved in 10 ml of tetrahydrofuran and 1.8 ml (1.8 mmol) of aqueous 1N lithium hydroxide solution are then added. The reaction medium is stirred for 15 hours at room temperature. After addition of water and acidification with acetic acid, the reaction medium is extracted with ethyl acetate. The organic phases are combined, dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with an 8/2 heptane/ethyl acetate mixture. 480 mg (82%) of 3-{3-butoxy-4-[3-(4-methanesulfonyloxy-3-methoxyphenyl)propyl]phenyl}propanoic acid are obtained after crystallization from a 2/8 isopropyl ether/pentane mixture.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with an 8/2 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-dca7d388e52c48fc9649ca8ccadca6f8
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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