Water → HCID 10482085, compound

HRID 2112066Notes

Reaction equation

HRID 2112066 reaction equation
[CH2:1]([N:5]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=1)[C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20]([O:22]C)=[O:21])=[CH:11][CH:10]=1)[CH:2]([CH3:4])[CH3:3].O.[OH-].[Li+]>C1COCC1>[CH2:1]([N:5]([CH2:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]([F:37])([F:38])[F:39])=[CH:34][CH:35]=1)[C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20]([OH:22])=[O:21])=[CH:13][CH:14]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68869926HCID 68869926, compound

Product 1

HCID 10482085HCID 10482085, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-{2-[4-(2-{isobutyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-ethoxy}benzoate (0.242 g, 0.455 mmol) was dissolved in a mixture of THF (freshly distilled)/water (2/1, 3 ml), lithium hydroxide (0.218 g, 0.909 mmol) was added. The reaction was performed in a single node microwave oven (5 min, 150 deg). THF was removed by evaporation. Water was added (10 ml) and the basic water phase was washed with diethyl ether (2×10 ml). Addition of HCl (2 ml, 1 M, pH 1). The water phase was extracted with two portions of DCM (20 ml), the organic phase was dried (MgSO4) and the solvent was removed by evaporation to give 0.135 g of 2-{2-[4-(2-{isobutyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]ethoxy}benzoic acid (yield 57.3%).

Workup

  1. additionwas added
  2. customThe reaction was performed in a single node microwave oven
  3. custom(5 min, 150 deg)
  4. customTHF was removed by evaporation
  5. additionWater was added (10 ml)
  6. washthe basic water phase was washed with diethyl ether (2×10 ml)
  7. additionAddition of HCl (2 ml, 1 M, pH 1)
  8. extractionThe water phase was extracted with two portions of DCM (20 ml)
  9. dry with materialthe organic phase was dried (MgSO4)
  10. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-c378e92f035a457c89dc9bb5c8eaf61c
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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