Dimethylformamide → HCID 66881558, compound

HRID 1893608Notes

Reaction equation

HRID 1893608 reaction equation
CN(C)C=O.Cl[CH2:7][C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:51])=[C:17]([N:19]([CH2:36][C:37]([N:39]([N:41]3[CH2:49][C:48]4[C:43](=[CH:44][CH:45]=[C:46]([F:50])[CH:47]=4)[CH2:42]3)[CH3:40])=[O:38])[CH2:20][C:21]([NH:23][CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH3:28])=[O:22])[CH:18]=2)[N:9]=1.[C:52]([O-:55])(=[O:54])[CH3:53].[Na+].C(OCC)(=O)C.CCCCCC>O>[C:52]([O:55][CH2:7][C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:51])=[C:17]([N:19]([CH2:36][C:37]([N:39]([N:41]3[CH2:49][C:48]4[C:43](=[CH:44][CH:45]=[C:46]([F:50])[CH:47]=4)[CH2:42]3)[CH3:40])=[O:38])[CH2:20][C:21]([NH:23][CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH3:28])=[O:22])[CH:18]=2)[N:9]=1)(=[O:54])[CH3:53]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 21226206Ethyl acetate hexaneHCID 123621071HCID 123621071, compound

Product 1

HCID 66881558HCID 66881558, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To N,N-dimethylformamide (40 ml) were added the compound (3.39 g, 5.15 mmol) of step A and sodium acetate (1.37 g, 16.7 mmol), and the mixture was stirred at 60° C. for 5 hr. After cooling to room temperature, ethyl acetate-hexane=1:1 mixed solvent and water were added to the reaction mixture, and the organic layer was extracted. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (3.15 g, yield 90%) as a pale-yellow amorphous solid

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe organic layer was extracted
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe solution was concentrated under reduced pressure
  7. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c261586a31bd4fea84a21cd875f575b4
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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