Water → HCID 53731379, compound

HRID 842272Notes

Reaction equation

HRID 842272 reaction equation
[H-].[Na+].[C:3]([O:6][CH2:7][C:8]([NH:21][C:22](=[O:24])[CH3:23])([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])[CH2:9][CH2:10][CH3:11])(=[O:5])[CH3:4].[CH2:25](Br)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].O>CN(C)C=O.O1CCCC1>[C:3]([O:6][CH2:7][C:8]([NH:21][C:22](=[O:24])[CH3:23])([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:9][CH2:10][CH3:11])(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 123691-BromoheptaneHCID 24758Sodium hydrideHCID 53753805HCID 53753805, compound

Product 1

HCID 53731379HCID 53731379, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (85 mg) in dimethylformamide (5 ml), a solution of 2-acetamido-2-(2-(2-hydroxyphenyl)ethyl)pentyl acetate (0.65 g) in dimethylformamide (5 ml) was added under ice-cooling and the mixture was stirred at room temperature for an hour. To the solution, a solution of heptyl bromide (0.42 g) in tetrahydrofuran (4 ml) was added. The mixture was stirred at the same temperature for 6 hours and left standing overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and a saturated brine and dried over magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; chloroform-methanol=12:1) to give the subject compound (0.36 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 6 hours
  3. waitleft
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous sodium hydrogencarbonate solution
  6. dry with materiala saturated brine and dried over magnesium sulfate
  7. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-90801a5219d44160a7ee9b969f169127
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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