Potassium Carbonate → HCID 59704816, compound

HRID 1716313Notes

Reaction equation

HRID 1716313 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[C:29]([O:34][CH3:35])(=[O:33])[C@@H:30]1[O:32][CH2:31]1.CCOCC.O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1>[OH:32][C@@H:30]([C:29]([O:34][CH3:35])=[O:33])[CH2:31][N:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:19]=[CH:20][C:3]([C:2]([F:1])([F:21])[F:22])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1)[S:15]([CH3:18])(=[O:16])=[O:17]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 9877347Methyl (2R)-2-oxiranecarboxylateHCID 21584184Diethylether waterHCID 59704780HCID 59704780, compound

Product 1

HCID 59704816HCID 59704816, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide (16.55 g, 50 mmol) from Step A, K2CO3 (17.3 g, 125 mmol), and benzyltriethylammonium chloride (1.135 g, 5 mmol) in dried 1,4-dioxane (75 mL) was added methyl(R)-glycidate (15.3 g, 150 mmol). The mixture was sealed and was heated to 70° C. for 24 h. The mixture was then poured into Et2O/H2O (200 mL/200 mL). The organic layer was washed with brine (200 mL), dried (Na2SO4), and filtered. After removal of solvent, the crude product was recrystallized from Et2O/hexane to give 17.8 g of the product (83%) as a pale brown solid. 1H NMR (300 MHz, CDCl3) δ 7.62 (d, J=9.0 Hz, 2H), 7.40 (d, J=9.0 Hz, 2H), 7.10 (d, J=9.0 Hz, 2H), 7.07 (d, J=9.0 Hz, 2H), 4.29 (d, J=6.0 Hz, 1H), 4.03-3.97 (m, 2H), 3.72 (s, 3H), 3.06 (s, 1H, OH), 3.05 (s, 3H); MS (EI) 456 (M++Na, 100), 434 (M++1). Anal. Calcd for C18H18F3NO6S: C, 49.88; H, 4.19; N, 3.23. Found: C, 50.00; H, 4.02; N, 3.22.

Workup

  1. customThe mixture was sealed
  2. washThe organic layer was washed with brine (200 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customAfter removal of solvent
  6. customthe crude product was recrystallized from Et2O/hexane

Sources & evidence

ORD record
ord-a19b8efafdbc48afb4076db45ffaee14
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

Loading…