Acetic Acid → HCID 86642713, compound

HRID 1361087Notes

Reaction equation

HRID 1361087 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][CH:35]2[CH2:37][CH2:36]2)=[CH:14][C:13]=1[O:38][CH3:39])(=[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][CH:35]2[CH2:37][CH2:36]2)=[CH:14][C:13]=1[O:38][CH3:39])(=[O:9])=[O:10])[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86642714HCID 86642714, compound

Product 1

HCID 86642713HCID 86642713, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

0.4 g (1 mmol) of lithium hydroxide monohydrate is added to a solution of 0.26 g (0.5 mmol) of corresponding methyl 3-(4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-3-cyclopropylmethoxyphenyl)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 (100%) of 3-(4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-3-cyclopropylmethoxyphenyl)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-05bf4992a94a427d8865a69fb2074f7a
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

Loading…