Lithium Hydroxide → 2-Ethoxy-3-{4-[2-(heptyl-p-tolylacetyl-amino)-ethyl]-phenyl}-propionic acid

HRID 47799Notes

Reaction equation

HRID 47799 reaction equation
C[O:2][C:3](=[O:35])[CH:4]([O:32][CH2:33][CH3:34])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:15](=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:8][CH:7]=1.[Li+].[OH-]>O1CCCC1>[CH2:33]([O:32][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:15](=[O:24])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)=[CH:8][CH:7]=1)[C:3]([OH:35])=[O:2])[CH3:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 698840912-Ethoxy-3-{4-[2-(heptyl-p-tolylacetyl-amino)-ethyl]-phenyl}-propionic acid methyl ester

Product 1

HCID 234312262-Ethoxy-3-{4-[2-(heptyl-p-tolylacetyl-amino)-ethyl]-phenyl}-propionic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-ethoxy-3-{4-[2-(heptyl-p-tolylacetyl-amino)-ethyl]-phenyl}-propionic acid methyl ester (21 mg, 0.044 mmol) and 1 M LiOH (0.131 mmol, 0.131 mL) in tetrahydrofuran (1 mL) was allowed to stir at room temperature for 24 hours. 2 N HCL was then added until the solution had a pH<2. After dilution with twice its volume in water, the aqueous layer was extracted with diethyl ether (2×). The organic layers were combined, washed with 2 M HCl (2×), dried over anhydrous sodium sulfate, and concentrated to give 2-ethoxy-3-{4-[2-(heptyl-p-tolylacetyl-amino)-ethyl]-phenyl}-propionic acid as a clear oil (19.5 mg, 95%).

Workup

  1. addition2 N HCL was then added until the solution
  2. extractionAfter dilution with twice its volume in water, the aqueous layer was extracted with diethyl ether (2×)
  3. washwashed with 2 M HCl (2×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e49004a1e3374736935232a8b945e422
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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