Hydrochloric Acid → HCID 22988731, compound

HRID 987331Notes

Reaction equation

HRID 987331 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:31])[CH:8]([O:28][CH2:29][CH3:30])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)C.Cl>O.O1CCCC1>[CH3:27][N:25]([CH3:26])[C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][O:16][C:13]2[CH:14]=[CH:15][C:10]([CH2:9][CH:8]([O:28][CH2:29][CH3:30])[C:7]([OH:31])=[O:6])=[CH:11][CH:12]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 53709700HCID 53709700, compound

Product 1

HCID 22988731HCID 22988731, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate (38 mg; 0.90 mmole) dissolved in water (2 ml) was added to a solution of 3-{4-[2-(4-dimethylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester (described in Example 99) (232 mg; 0.60 mmole) in tetrahydrofuran (6 ml). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was acidified with hydrochloric acid (2 M) to pH 5. Tetrahydrofuran was evaporated in vacuo, water (5 ml) was added and the mixture was extracted with ethyl acetate (10+5 ml), dried (sodium sulfate) and the solvent was evaporated in vacuo. Purification by filtration on silica gel gave 180 mg (yield 84%) of 3-{4-[2-(4-dimethylaminophenyl)ethoxy]phenyl}-2-ethoxypropanoic acid.

Workup

  1. customTetrahydrofuran was evaporated in vacuo, water (5 ml)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (10+5 ml)
  4. dry with materialdried (sodium sulfate)
  5. customthe solvent was evaporated in vacuo
  6. customPurification
  7. filtrationby filtration on silica gel

Sources & evidence

ORD record
ord-3ab7e6ca54ab4c5d92b2ec4958107bd5
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

Loading…