Lithium Hydroxide → HCID 23431239, compound

HRID 47803Notes

Reaction equation

HRID 47803 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]([N:17]([CH3:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])=[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]([N:17]([CH3:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:16])=[CH:8][CH:7]=1)[C:3]([OH:35])=[O:2])[CH3:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69885320HCID 69885320, compound

Product 1

HCID 23431239HCID 23431239, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-ethoxy-3-{4-[2-(1-heptyl-3-methyl-3-phenyl-ureido)-ethyl]-phenyl}-propionic acid methyl ester (98 mg, 0.20 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-(1-heptyl-3-methyl-3-phenyl-ureido)-ethyl]-phenyl}-propionic acid as a clear oil (73 mg, 78%).

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-4770f79a9e29433d9940b088a0953414
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

Loading…