Hydrochloric Acid → HCID 68986100, compound

HRID 2249647Notes

Reaction equation

HRID 2249647 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:9]=[CH:8][C:7]=1[CH:17]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[C:18]1[CH:19]=[CH:20][C:21]([O:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[C:22]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])[CH:23]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].O.Cl>C(O)C.C(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:9]=[CH:8][C:7]=1[CH:17]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[C:18]1[CH:19]=[CH:20][C:21]([O:31][CH2:32][CH:33]([CH3:34])[CH3:35])=[C:22]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:23]=1)[CH:2]([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68983462HCID 68983462, compound

Product 1

HCID 68986100HCID 68986100, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

In 7 ml of ethanol is dissolved 1.26 g of ethyl 3-(5-{(2,4-diisobutoxyphenyl)[(methylsulfonyl)-amino]methyl}-2-isobutoxyphenyl)propanoate, to which is added 1.3 ml of 5 mol/L solution of sodium hydroxide. The mixture is stirred at ambient temperature for one hour. Water and chloroform are added to the reaction mixture, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1) to obtain 0.92 g of 3-(5-{(2,4-diisobutoxyphenyl)[(methylsulfonyl)amino]methyl}-2-isobutoxyphenyl)propanoic acid as a light yellow oily product.

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe residue thus obtained
  6. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0c6262a810914b4fbf1c8e4295362562
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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