Lithium Hydroxide → HCID 23431232, compound

HRID 47798Notes

Reaction equation

HRID 47798 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]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[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]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[O:16])=[CH:8][CH:7]=1)[C:3]([OH:35])=[O:2])[CH3:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57438212HCID 57438212, compound

Product 1

HCID 23431232HCID 23431232, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-ethoxy-3-{4-[2-(1-heptyl-3-p-tolyl-ureido)-ethyl]-phenyl}-propionic acid methyl ester (40 mg, 0.083 mmol) and 1 M LiOH (0.25 mmol, 0.25 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 a crude oil. The crude oil was chromatographed on silica gel (2% methanol/methylene chloride gradient to 15% methanol/methylene chloride) to give 2-ethoxy-3-{4-[2-(1-heptyl-3-p-tolyl-ureido)-ethyl]-phenyl}-propionic acid as a white waxy-solid (32 mg, 82%).

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 crude oil was chromatographed on silica gel (2% methanol/methylene chloride gradient to 15% methanol/methylene chloride)

Sources & evidence

ORD record
ord-d2106e1372cf4032b2b43ab5775501ab
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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