Methyl iodide → HCID 57794739, compound

HRID 2099272Notes

Reaction equation

HRID 2099272 reaction equation
IC.[C:3]1([C@@:9]2([CH2:21][NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH2:11][C@H:10]2[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:32](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:32][N:22]([CH2:21][C@:9]1([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:11][C@H:10]1[CH2:12][O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57794730HCID 57794730, compound

Product 1

HCID 57794739HCID 57794739, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Iodomethane (2.12 g, 14.9 mmol, 4 eq) was added portionwise to N-[((1R,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropyl)methyl]benzenesulfonamide (1.71 g, 3.74 mmol, 1 eq), accessed via the method of preparation 5B, in 7 mL DMF with potassium carbonate (1.03 g, 7.48 mmol, 2 eq) over 6 h at 80° C. Following addition, the reaction mixture was stirred 16 h at 80° C. The reaction mixture was diluted with EtOAc, washed successively with saturated aqueous NaHCO3, water (4×) and brine, dried over MgSO4, filtered and concentrated to give a brown oil. The crude material was purified by flash chromatography (SiO2, eluted successively with hexanes and EtOAc/hexanes (1:4)) to give the title product (1.57 g, 100%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.58-7.21 (m, 15H), 4.26 (ABq, J=26.5, 11.7 Hz, 2H), 3.50 (d, J=14.0 Hz, 1H), 3.23-3.20 (m, 1H), 2.94-2.89 (m, 2H), 2.54 (s, 3H), 1.39 (m, 1H), 1.10 (m, 1H), 0.92 (m, 1H). ES-LCMS m/z 444.3 (M+Na).

Workup

  1. additionaddition
  2. washwashed successively with saturated aqueous NaHCO3, water (4×) and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a brown oil
  7. customThe crude material was purified by flash chromatography (SiO2
  8. washeluted successively with hexanes and EtOAc/hexanes (1:4))

Sources & evidence

ORD record
ord-e0cff9b2c1d7426d8bbea9d8bf5d3652
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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