Lithium Hydroxide → 3-(4-{2-[3-(2,4-Dimethoxy-phenyl)-1-heptyl-ureido]-ethyl}-phenyl)-2-ethoxy-propionic acid

HRID 47795Notes

Reaction equation

HRID 47795 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([O:35][CH2:36][CH3:37])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=2[O:26][CH3:27])=[O:16])=[CH:8][CH:7]=1.[Li+].[OH-]>O1CCCC1>[CH3:27][O:26][C:19]1[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:18]=1[NH:17][C:15](=[O:16])[N:14]([CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([O:35][CH2:36][CH3:37])[C:3]([OH:38])=[O:2])=[CH:7][CH:8]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69884386HCID 69884386, compound

Product 1

HCID 234311923-(4-{2-[3-(2,4-Dimethoxy-phenyl)-1-heptyl-ureido]-ethyl}-phenyl)-2-ethoxy-propionic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-{2-[3-(2,4-dimethoxy-phenyl)-1-heptyl-ureido]-ethyl}-phenyl)-2-ethoxy-propionic acid methyl ester (249 mg, 0.47 mmol) and 1 M LiOH (1.41 mmol, 1.41 mL) in tetrahydrofuran (2 mL) was allowed to stir at room temperature for 16 hours. The solution was quenched by the addition of 2 N HCl 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 3-(4-{2-[3-(2,4-dimethoxy-phenyl)-1-heptyl-ureido]-ethyl}-phenyl)-2-ethoxy-propionic acid as a clear oil (229 mg, 95%).

Workup

  1. customThe solution was quenched by the addition of 2 N HCl 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-8f45485508e74bc3a7c8c78d757f4ffa
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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