Water → HCID 18551278, compound

HRID 1266534Notes

Reaction equation

HRID 1266534 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:23]=[CH:22][C:10]([O:11][C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:9][CH:8]=1.Br[CH2:25][C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[CH:31][C:30]=1[CH3:41])=[O:27].C(=O)(O)[O-].[Na+].O>CN(C)C=O>[CH:35]1([C:32]2[CH:33]=[CH:34][C:29]([NH:28][C:26](=[O:27])[CH2:25][N:5]([CH2:6][C:7]3[CH:23]=[CH:22][C:10]([O:11][C:12]([CH3:21])([CH3:20])[C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])=[CH:9][CH:8]=3)[CH2:4][CH2:3][O:2][CH3:1])=[C:30]([CH3:41])[CH:31]=2)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 22708147HCID 22708147, compoundHCID 22708166HCID 22708166, compound

Product 1

HCID 18551278HCID 18551278, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

0.303 g (0.94 mmol) of tert-butyl 2-(4-{[(2-methoxyethyl)amino]methyl}phenoxy)-2-methylpropanoate (Example III-33) is initially charged in 5 ml of dimethylformamide. At room temperature, 0.319 g (1.03 mmol) of 2-bromo-N-(4-cyclohexyl-2-methylphenyl)acetamide (Example III-19) and 0.086 g (1.03 mmol) of sodium bicarbonate are added. The mixture is stirred at 90° C. for 2 hours. The reaction mixture is then allowed to cool, and water is added. The mixture is extracted with ethyl acetate and the organic phase is washed with water and saturated sodium chloride solution. The organic phase is dried over sodium sulphate and freed from the solvent under reduced pressure. The residue is purified chromatographically on silica gel (cyclohexane/ethyl acetate 3:1) and the product is dried under reduced pressure. This gives 0.464 g (90% of theory) of the title compound.

Workup

  1. customAt room temperature
  2. temperatureto cool
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe organic phase is washed with water and saturated sodium chloride solution
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. customThe residue is purified chromatographically on silica gel (cyclohexane/ethyl acetate 3:1)
  7. customthe product is dried under reduced pressure

Sources & evidence

ORD record
ord-c67de4d347a2428abf3ae7fa5967d9f8
Source dataset
uspto-grants-2003_04
Patent number
US06548538B2

Reaction notes

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