Hydrochloric Acid → HCID 18448299, compound

HRID 1269692Notes

Reaction equation

HRID 1269692 reaction equation
[CH2:1]([N:5]([CH2:20][C:21]1[CH:33]=[CH:32][C:24]([O:25][CH2:26][C:27]([O:29]CC)=[O:28])=[C:23]([CH3:34])[CH:22]=1)[C:6]1[C:7]([CH3:19])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>C1COCC1.O>[CH2:1]([N:5]([CH2:20][C:21]1[CH:33]=[CH:32][C:24]([O:25][CH2:26][C:27]([OH:29])=[O:28])=[C:23]([CH3:34])[CH:22]=1)[C:6]1[C:7]([CH3:19])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58622877HCID 58622877, compound

Product 1

HCID 18448299HCID 18448299, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (4-{[butyl(2,4′-dimethyl-1,1′-biphenyl-3-yl)amino]methyl}-2-methylphenoxy)acetate (12.7 g, 27.6 mmol) was dissolved in THF (210 mL) and water (70 ml) was added, followed by 2M aq. NaOH (61 mL, 122 mmol). The reaction was stirred at room temperature for 1/2 hr and then evaporated to give a white slurry. The suspension was diluted with water (100 mL) and pH adjusted to pH7 with 2M aq HCl. EtOAc (200 mL) the aqueous layer was separated and extracted with EtOAc (2×100 mL). The combined organics were washed with brine (200 mL), dried (Na2SO4) and concentrated In vacuo to give the title compound as a white foam (11.1 g).

Workup

  1. customevaporated
  2. customto give a white slurry
  3. customEtOAc (200 mL) the aqueous layer was separated
  4. extractionextracted with EtOAc (2×100 mL)
  5. washThe combined organics were washed with brine (200 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated In vacuo

Sources & evidence

ORD record
ord-0897a9c66f724b238cde263b17e68c31
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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