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

HRID 47796Notes

Reaction equation

HRID 47796 reaction equation
C[O:2][C:3](=[O:36])[CH:4]([O:33][CH2:34][CH3:35])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])=[O:16])=[CH:8][CH:7]=1.[Li+].[OH-]>O1CCCC1>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[NH:17][C:15](=[O:16])[N:14]([CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][CH:4]([O:33][CH2:34][CH3:35])[C:3]([OH:36])=[O:2])=[CH:11][CH:10]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 698843623-(4-{2-[3-(2,4-Difluoro-phenyl)-1-heptyl-ureido]-ethyl}-phenyl)-2-ethoxy-propionic acid methyl ester

Product 1

HCID 234312283-(4-{2-[3-(2,4-Difluoro-phenyl)-1-heptyl-ureido]-ethyl}-phenyl)-2-ethoxy-propionic acidYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-{2-[3-(2,4-difluoro-phenyl)-1-heptyl-ureido]-ethyl}-phenyl)-2-ethoxy-propionic acid methyl ester (44 mg, 0.087 mmol) and 1 M LiOH (0.26 mmol, 0.26 mL) in tetrahydrofuran (2 mL) was allowed to stir at room temperature for 94 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 a crude oil. The oil was chromatographed on silica gel (15% methanol/methylene chloride) to give 3-(4-{2-[3-(2,4-difluoro-phenyl)-1-heptyl-ureido]-ethyl}-phenyl)-2-ethoxy-propionic acid as a white waxy-solid (26.3 mg, 62%).

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 to a crude oil
  6. customThe oil was chromatographed on silica gel (15% methanol/methylene chloride)

Sources & evidence

ORD record
ord-b2e73fdd251847daa7c551fd1fc98d67
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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