Dimethylformamide → HCID 54501436, compound

HRID 1602507Notes

Reaction equation

HRID 1602507 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:44]=[CH:45][CH:46]=2)[C:15]([NH:17][C:18]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][S:34]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:28]=[CH:27][C:19]=2[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:16])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:49]N(C)C=O.CI>O>[C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:44]=[CH:45][CH:46]=2)[C:15]([N:17]([C:18]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][S:34]([C:37]3[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=3)(=[O:36])=[O:35])[CH:28]=[CH:27][C:19]=2[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:49])=[O:16])[S:8][CH:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53953312HCID 53953312, compound

Product 1

HCID 54501436HCID 54501436, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, ethyl 2-[3-[(4-tert-butyl-2-thiazolyl)methoxy]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetate (266 mg, 0.39 mmol) was added to a mixture of 60% sodium hydride (19 mg, 0.48 mmol) and dimethylformamide (2 ml), and the reaction solution was stirred at room temperature for 1 hour. The reaction solution was again cooled with ice, methyl iodide (29 μl, 0.47 mmol) was added, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution and the product formed was extracted with toluene. The extract was washed with water and brine in that order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (eluent=chloroform:methanol=50:1) to give ethyl 2-[N-[3-[(4-tert-butyl-2-thiazolyl)methoxy]benzoyl]-N-methylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetate (213 mg, 0.31 mmol, 78%).

Workup

  1. temperatureUnder ice-cooling
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. customthe product formed
  5. extractionwas extracted with toluene
  6. washThe extract was washed with water and brine in that order
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThereafter, the resulting residue was purified by silica gel column chromatography (eluent=chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-d79149df193742a78ce2767543745a3d
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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