Water → HCID 18679733, compound

HRID 1633720Notes

Reaction equation

HRID 1633720 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[C:7]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:6][CH:5]=[CH:4][C:3]1=2.[H-].[Na+].[CH3:19][O:20][CH2:21]Cl.O>CN(C=O)C>[CH3:19][O:20][CH2:21][N:12]([C:7]1[C:8]2[CH2:9][CH2:10][CH2:11][C:2](=[O:1])[C:3]=2[CH:4]=[CH:5][CH:6]=1)[S:13]([CH3:16])(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 18679763HCID 18679763, compound

Product 1

HCID 18679733HCID 18679733, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 15A (4.0 g, 17 mmol) in anhydrous DMF (40 mL) under a nitrogen atmosphere was treated with a 60% dispersion of sodium hydride (0.74 g, 18 mmol) in portions over 5 minutes, stirred for 45 minutes, cooled to 0° C., treated dropwise with chloromethyl methyl ether (1.3 mL, 18 mmol), stirred at ambient temperature for 2 hours, treated with cold water (250 mL) and extracted with diethyl ether (3×). The combined diethyl ether extracts were washed with water, washed with brine, dried (MgSO4), filtered and concentrated. Purification of the residue on silica gel with 1:1 hexanes:ethyl acetate provided the desired product.

Workup

  1. stirringstirred at ambient temperature for 2 hours
  2. extractionextracted with diethyl ether (3×)
  3. washThe combined diethyl ether extracts were washed with water
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue on silica gel with 1:1 hexanes

Sources & evidence

ORD record
ord-bffecbfcda2f4e2189340cf41d55f066
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

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