Water → HCID 21716317, compound

HRID 1385909Notes

Reaction equation

HRID 1385909 reaction equation
Br[C:2]([CH3:24])([CH3:23])[C:3]([NH:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:10]=1)[OH:8])=[O:4].[H-].[Na+].O>CN(C)C=O>[CH:18]1([O:17][C:11]2[CH:10]=[C:9]([CH:7]3[O:8][C:2]([CH3:24])([CH3:23])[C:3](=[O:4])[NH:5][CH2:6]3)[CH:14]=[CH:13][C:12]=2[O:15][CH3:16])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 21716350HCID 21716350, compound

Product 1

HCID 21716317HCID 21716317, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A crude product (1.03 g) of 2-(2-bromo-2-methylpropionamido)-1-(3-cyclopentyloxy-4-methoxyphenyl)ethanol and sodium hydride (60%) (0.23 g) were stirred in dry dimethylformamide (40 ml) at room temperature for one night. Water was added to the reaction solution obtained and the solution was extracted with ethyl acetate. Next, the extract was washed several times with water and was dried over anhydrous sodium sulfate, then the solvent was evaporated in vacuo to obtain a crude product. The crude product obtained was purified by flash chromatography (SiO2: eluted with gradient of range from 33% ethyl acetate/hexane to 75% ethyl acetate/hexane) to obtain the above-described compound 0.17 g (yield 21.1%) as a light yellow solid.

Workup

  1. customobtained
  2. extractionthe solution was extracted with ethyl acetate
  3. washNext, the extract was washed several times with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customto obtain a crude product
  7. customThe crude product obtained
  8. customwas purified by flash chromatography (SiO2: eluted with gradient of range from 33% ethyl acetate/hexane to 75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-75ff13e28bd44d77982e3fad0e4a60e3
Source dataset
uspto-grants-2001_07
Patent number
US06265402B1

Reaction notes

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