Potassium Carbonate → HCID 118060108, compound

HRID 632530Notes

Reaction equation

HRID 632530 reaction equation
[C:1]([O:5][C:6]([NH:8][S:9]([NH:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](=[O:22])([O-])[O-].[K+].[K+].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1>[I-].[Na+].CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH2:31][C:30]1[CH:33]=[CH:34][C:27]([O:22][CH3:19])=[CH:28][CH:29]=1)[S:9]([N:12]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:31][C:30]1[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 10636611HCID 10636611, compound

Product 1

HCID 118060108HCID 118060108, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Ethyl ({[(tert-butoxycarbonyl)amino]sulfonyl}amino)acetate (1.00 g, 4.0 mmol) was mixed with N,N-dimethylformamide (DMF, 6.0 mL) and stirred at room temperature. Sodium iodide (0.01 g, 0.1 mmol, 0.025 equiv.), potassium carbonate (2.40 g, 20 mmol, 5.0 equiv.) and para-methoxybenzyl chloride (2.64 mL, 19.5 mmol, 4.875 equiv.) were added to the mixture. This reaction was warmed to 80° C. and stirred at 80° C. for 2 h. LCMS indicated reaction completion. The reaction was cooled to room temperature and filtered through Celite. The Celite bed was washed with dichloromethane and the combined organic filtrates were concentrated. The concentrated residue was dissolved in dichloromethane (20 mL) and washed with sodium bicarbonate (5×12 mL) and brine. The organic layer was dried over sodium sulfate and concentrated. The residue was purified on silica gel (0-40% ethyl acetate/hexane gradient elution) to give the desired product (1.39 g, 80%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.22 (m, 2H), 7.14 (m, 2H), 6.88 (m, 4H), 4.64 (s, 2H), 4.33 (s, 2H), 4.03 (q, 2H, J=7.1 Hz), 3.92 (s, 2H), 3.72 (s, 3H), 3.71 (s, 3H), 1.39 (s, 9H), 1.14 (t, 3H, J=7.1 Hz).

Workup

  1. temperatureThis reaction was warmed to 80° C.
  2. stirringstirred at 80° C. for 2 h
  3. customreaction completion
  4. temperatureThe reaction was cooled to room temperature
  5. filtrationfiltered through Celite
  6. washThe Celite bed was washed with dichloromethane
  7. concentrationthe combined organic filtrates were concentrated
  8. dissolutionThe concentrated residue was dissolved in dichloromethane (20 mL)
  9. washwashed with sodium bicarbonate (5×12 mL) and brine
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was purified on silica gel (0-40% ethyl acetate/hexane gradient elution)

Sources & evidence

ORD record
ord-e256e5841748431a811bfd598aca522d
Source dataset
uspto-grants-2016_04
Patent number
US09321755B2

Reaction notes

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