Lithium Hydroxide → 2-Ethoxy-3-(4-{2-[heptyl-(1-p-tolyl-cyclopropanecarbonyl)-amino]-ethyl}-phenyl)-propionic acid

HRID 47802Notes

Reaction equation

HRID 47802 reaction equation
C[O:2][C:3](=[O:37])[CH:4]([O:34][CH2:35][CH3:36])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:15]([C:17]2([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[CH2:19][CH2:18]2)=[O:16])=[CH:8][CH:7]=1.[Li+].[OH-]>O1CCCC1>[CH2:35]([O:34][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:15]([C:17]2([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[CH2:19][CH2:18]2)=[O:16])=[CH:8][CH:7]=1)[C:3]([OH:37])=[O:2])[CH3:36]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69884464HCID 69884464, compound

Product 1

HCID 234312432-Ethoxy-3-(4-{2-[heptyl-(1-p-tolyl-cyclopropanecarbonyl)-amino]-ethyl}-phenyl)-propionic acidYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-ethoxy-3-(4-{2-[heptyl-(1-p-tolyl-cyclopropanecarbonyl)-amino]-ethyl}-phenyl)-propionic acid methyl ester (94 mg, 0.185 mmol) and 1 M LiOH (0.60 mmol, 0.60 mL) in tetrahydrofuran (1 mL) was allowed to stir at room temperature for 16 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-(1-p-tolyl-cyclopropanecarbonyl)-amino]-ethyl}-phenyl)-propionic acid as a clear oil (60 mg, 66%).

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-a948da155a7941169cc2c4194d15c399
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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