Methyl iodide → HCID 68818472, compound

HRID 736745Notes

Reaction equation

HRID 736745 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:9]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:24]([CH3:32])[CH:23]=3)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:8][O:7][CH2:6]1)=[O:4].[C:33](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH:9]([N:10]([CH3:33])[S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:24]([CH3:32])[CH:23]=3)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:8][O:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68820697HCID 68820697, compound

Product 1

HCID 68818472HCID 68818472, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a slurry of 0.3 g (0.658 mmol) of 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-furan-3-carboxylic acid methyl ester (Example 26, Step 1) and potassium carbonate (0.182 g, 1.32 mmol) in DMF (10 mL) was added iodomethane (0.103 g, 0.723 mmol). The reaction was stirred at 25° C. for 19 h. The DMF was removed in vacuo and the resulting oil was diluted with ethyl acetate (100 mL). The organics were washed with water (2×30 mL) and saturated aqueous sodium chloride (30 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide a crude oil (0.42 g) that was purified by Biotage Flash 40S chromatography, eluting with 2:1 ethyl acetate:hexanes, to afford 4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-furan-3-carboxylic acid methyl ester as an amorphous white solid (0.270 g, 87%). MS: 471 (M+H)+.

Workup

  1. customThe DMF was removed in vacuo
  2. additionthe resulting oil was diluted with ethyl acetate (100 mL)
  3. washThe organics were washed with water (2×30 mL) and saturated aqueous sodium chloride (30 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a crude oil (0.42 g) that
  8. customwas purified by Biotage Flash 40S chromatography
  9. washeluting with 2:1 ethyl acetate

Sources & evidence

ORD record
ord-0feabdd9c2a24a57a0bb0abd2a3e765e
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

Loading…