Acetic Acid → HCID 25123287, compound

HRID 1361085Notes

Reaction equation

HRID 1361085 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][CH:38]=[C:37]([F:41])[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][CH:38]=[C:37]([F:41])[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 86642711HCID 86642711, compound

Product 1

HCID 25123287HCID 25123287, compoundYield 82.3%

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-(3-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. 0.23 g (77%) of 3-[4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-3-(3-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-f40002fc8e31485cb96e22fa7fcef9d6
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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