Methyl iodide → Ammonium Acetate

HRID 1470010Notes

Reaction equation

HRID 1470010 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH2:21][CH2:22][O:23][CH3:24])/[C:5](=[N:9]/[C:10]([C:12]23[CH2:19][CH:18]4[CH2:20][CH:14]([CH2:15][CH:16]2[CH2:17]4)[CH2:13]3)=[O:11])/[S:6][C:7]=1[CH3:8].[H-].[Na+].CI.[O:29]1CCC[CH2:30]1>>[C:22]([O-:23])(=[O:29])[CH3:21].[NH4+:4].[CH3:24][O:23][CH2:22][CH2:21][N:4]1[C:3]([CH2:2][O:1][CH3:30])=[C:7]([CH3:8])[S:6]/[C:5]/1=[N:9]\[C:10]([C:12]12[CH2:19][CH:18]3[CH2:20][CH:14]([CH2:15][CH:16]1[CH2:17]3)[CH2:13]2)=[O:11]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 178495824HCID 178495824, compound

Product 2

HCID 517165Ammonium AcetateHCID 178495822HCID 178495822, compound

Procedure

To a solution of Example 128 (32.0 mg, 0.09 mmol) in tetrahydrofuran (3 mL) was added sodium hydride (Aldrich, 3.7 mg, 0.15 mmol) and methyl iodide (Aldrich, 15.6 mg, 0.11 mmol). The reaction mixture was stirred at room temperature overnight then quenched with saturated aqueous NaHCO3 and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative high pressure liquid chromatography on a waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.47-1.64 (m, 4H), 1.62-1.84 (m, 4H), 2.03-2.18 (m, 2H), 2.27 (s, 2H), 2.27 (s, 3H), 2.50-2.62 (m, 1H), 3.24 (d, J=1.4 Hz, 3H), 3.24 (s, 3H), 3.64 (t, J=5.8 Hz, 2H), 4.26 (t, J=5.8 Hz, 2H), 4.45 (s, 2H); MS (ESI+) m/z 365 (M+H)+; Anal. Calculated for C19H28N2O3S: C, 62.61; H, 7.74; N, 7.69. Found: C, 62.62; H, 7.73; N, 7.85.

Workup

  1. customthen quenched with saturated aqueous NaHCO3
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative high pressure liquid chromatography on a waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size)

Sources & evidence

ORD record
ord-48782d72da254beea33783e0ee1ef856
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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