Dimethyl Sulfate → HCID 69961590, compound

HRID 429280Notes

Reaction equation

HRID 429280 reaction equation
[C:1]1([O:14][C:15]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]([OH:25])=[O:24])[CH2:18]2)=[O:16])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:26](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[C:1]1([O:14][C:15]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]([O:25][CH3:26])=[O:24])[CH2:18]2)=[O:16])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 18375821HCID 18375821, compound

Product 1

HCID 69961590HCID 69961590, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3.00 g of 4-fluorenyloxycarbonylmorpholine-2-carboxylic acid in 150 mL of acetone was added 1.77 g of potassium carbonate and 1.33 g of dimethyl sulfate. The mixture was heated to reflux and stirred at this temperature for 6 h, then cooled, filtered, and concentrated. The residue was dissolved in 125 mL of Et2O and washed with 50 mL each of saturated NaHCO3, water, and brine. The organic phase was dried over MgSO4 and concentrated to yield 3.10 g of the title compound, which was used without further purification. 1H NMR (500 MHz, CDCl3): δ7.76 (d, J=7.6 Hz, 2H), 7.57 (br d, J=6.6 Hz, 2H), 7.40 (t, J=7.3 Hz, 2H), 7.32 (t, J=7.6 Hz, 2H), 4.51 (br s, 2H), 4.25 (br t, J=6.2 Hz, 1H), 3.90-4.10 (m, 4H), 3.80 (s, 3H), 3.40-3.70 (m, 1H), 3.04-3.23 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 125 mL of Et2O
  7. washwashed with 50 mL each of saturated NaHCO3, water, and brine
  8. dry with materialThe organic phase was dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a07efad840894abcb093d821dff40c82
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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