Hydrochloric Acid → HCID 57719936, compound

HRID 1985388Notes

Reaction equation

HRID 1985388 reaction equation
C([O:3][C:4](=[O:31])[C@@H:5]([O:27][CH:28]([CH3:30])[CH3:29])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C@H:15]([OH:26])[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[CH:8]=1)C.[OH-].[Na+].Cl>C(O)C>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[O:17][CH2:16][C@@H:15]([OH:26])[CH2:14][O:13][C:9]1[CH:8]=[C:7]([CH2:6][C@H:5]([O:27][CH:28]([CH3:29])[CH3:30])[C:4]([OH:31])=[O:3])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57719507HCID 57719507, compound

Product 1

HCID 57719936HCID 57719936, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

220 mg of 3-{3-[3-(2,4-Dichlorophenoxy)-2(S)-hydroxypropoxy]phenyl}-2(S)-isopropoxypropanoic acid ethyl ester was dissolved in 4 ml of ethanol, followed by adding 1 ml of 1N sodium hydroxide. After standing as it was at room temperature for 4 hours, the solution was neutralized with 1N hydrochloric acid and extracted with ethylacetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 200 mg of the title compound as a colorless oil in the 3:2→2:3 hexane-ethyl acetate fraction.

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b89668d6da35410f874b682df88fd7c4
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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