Water → HCID 20437853, compound

HRID 1980054Notes

Reaction equation

HRID 1980054 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:5]1[CH:17]([OH:25])[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1.[CH3:26][O:27][CH2:28][CH2:29][O:30][CH2:31]Cl.O>CCCCCC.CN(C)C=O>[O:3]=[C:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:11])[CH:5]1[CH:17]([O:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 13057043HCID 13057043, compound

Product 1

HCID 20437853HCID 20437853, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To 0.13 g (0.0054 mole) of NaH (0.22 g of a 61% dispersion in oil, washed with hexane) in 10 ml of dimethylformamide (DMF) was added 1.6 g of 35 in 20 ml of dry DMF, and the mixture stirred at 0° C. for 30 minutes. A solution of 0.67 g (0.0055 mole) of (2-methoxyethoxy)methyl chloride in 5 ml of dry DMF was added and the mixture allowed to warm to room temperature, stirred for 1 hour, and poured into 50 ml of water. The product was extracted into ethyl acetate and the extract washed with brine and dried over MgSO4. After filtration, the solvent was removed at reduced pressure and the residue triturated with hexane and filtered to give the title compound.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 hour
  3. extractionThe product was extracted into ethyl acetate
  4. washthe extract washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed at reduced pressure
  8. customthe residue triturated with hexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-13bbc92259404f7ebe85cd4b7464fff6
Source dataset
uspto-grants-1984_11
Patent number
US04483988

Reaction notes

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