Hydrochloric Acid → HCID 86630049, compound

HRID 2249645Notes

Reaction equation

HRID 2249645 reaction equation
[NH2:1][C:2](=[O:41])[CH2:3][O:4][N:5]=[C:6]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[CH:27][C:26]=1[O:36][CH2:37][CH:38]([CH3:40])[CH3:39])[C:7]1[CH:8]=[CH:9][C:10]([O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[C:11]([CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH:12]=1.[OH-].[Na+].C(Cl)(Cl)Cl.Cl>C(O)C.O>[NH2:1][C:2](=[O:41])[CH2:3][O:4][N:5]=[C:6]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH:33]([CH3:34])[CH3:35])=[CH:27][C:26]=1[O:36][CH2:37][CH:38]([CH3:40])[CH3:39])[C:7]1[CH:8]=[CH:9][C:10]([O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[C:11]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 86630048HCID 86630048, compound

Product 1

HCID 86630049HCID 86630049, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 10 ml of ethanol is dissolved 1.08 g of ethyl 3-{5-[[(2-amino-2-oxoethoxy)imino](2,4-diisobutoxyphenyl)methyl]-2-isobutoxyphenyl}propanoate, to which is added 1.1 ml of 5 mol/L sodium hydroxide solution. The mixture is stirred at ambient temperature for 3 hours. Chloroform and water 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 thus obtained 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; chloroform:ethanol=10:1) to obtain 0.68 g of 3-{5-[[(2-amino-2-oxoethoxy)imino](2,4-diisobutoxyphenyl)methyl]-2-isobutoxyphenyl}propanoic acid as a white foaming product.

Workup

  1. customthe organic layer is separated
  2. customThe organic layer thus obtained
  3. washis washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1)

Sources & evidence

ORD record
ord-dfde23599bfb4e07a8c459447540f582
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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