Hydrochloric Acid → HCID 22988779, compound

HRID 987315Notes

Reaction equation

HRID 987315 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:35])[CH:8]([O:32][CH2:33][CH3:34])[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]([C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH3:26])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)C.Cl>O.O1CCCC1>[CH2:33]([O:32][CH:8]([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]([C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH3:26])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)[C:7]([OH:35])=[O:6])[CH3:34]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 54418983HCID 54418983, compound

Product 1

HCID 22988779HCID 22988779, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate (62 mg; 1.48 mmole) dissolved in water (2 ml) was added to a solution of 2-ethoxy-3-(4-{2-[4-(isobutyryl-N-methylamino)phenyl]ethoxy}phenyl)propanoic acid ethyl ester (described in Example 72) (435 mg; 0.98 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 4. Tetrahydrofuran was evaporated in vacuo, water (5 ml) was added and the mixture was extracted with ethyl acetate (10 ml). The organic phase was dried (sodium sulfate) and solvent was evaporated in vacuo to give 398 mg (yield 98%) of 2-ethoxy-3-(4-{2-[4-(isobutyryl-N-methylamino)phenyl]ethoxy}phenyl)propanoic acid.

Workup

  1. customTetrahydrofuran was evaporated in vacuo, water (5 ml)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (10 ml)
  4. dry with materialThe organic phase was dried (sodium sulfate) and solvent
  5. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-19226459a8e941dbbae9ec7cd2af64d1
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

Loading…