Acetic Acid → HCID 25123288, compound

HRID 1361086Notes

Reaction equation

HRID 1361086 reaction equation
O.[OH-].[Li+].[CH2:4]([S:8]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[CH:23][C:22]=2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)=[CH:14][C:13]=1[O:42][CH3:43])(=[O:10])=[O:9])[CH2:5][CH2:6][CH3:7].O.C(O)(=O)C>O1CCCC1.CO.O>[CH2:4]([S:8]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:23][C:22]=2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)=[CH:14][C:13]=1[O:42][CH3:43])(=[O:9])=[O:10])[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86642712HCID 86642712, compound

Product 1

HCID 25123288HCID 25123288, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

0.4 g (1 mmol) of lithium hydroxide monohydrate is added to a solution of 0.3 g (0.5 mmol) of corresponding methyl 3-[4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-3-(4-fluorobenzyloxy)phenyl]propanoate in 10 ml of a tetrahydrofuran/methanol/water mixture (5/1/1). The reaction medium is stirred at room temperature for 15 hours, treated with water, acidified to pH 4 with acetic acid and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and concentrated. The residue obtained is purified by chromatography on a column of silica eluted with a 97/3 dichloromethane/methanol mixture. 0.24 g (85%) of 3-[4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-3-(4-fluorobenzyloxy)phenyl]propanoic acid is obtained in the form of a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a 97/3 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-16d5d707a2d647e59a24b66cf0ae3802
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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