Methyl iodide → HCID 19759894, compound

HRID 1586861Notes

Reaction equation

HRID 1586861 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[C:13]([NH:17][S:18]([C:21]1[S:25][C:24]2[S:26](=[O:34])(=[O:33])[CH:27]([C:29]([O:31]C)=[O:30])[CH2:28][C:23]=2[CH:22]=1)(=[O:20])=[O:19])([CH3:16])([CH3:15])[CH3:14].CI>C1COCC1.CCCCCC>[C:13]([NH:17][S:18]([C:21]1[S:25][C:24]2[S:26](=[O:33])(=[O:34])[C:27]([CH3:1])([C:29]([OH:31])=[O:30])[CH2:28][C:23]=2[CH:22]=1)(=[O:19])=[O:20])([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 19759914HCID 19759914, compoundHCID 178418339Butyllithium

Product 1

HCID 19759894HCID 19759894, compoundYield 118.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of diisopropylamine (4.44 mL, 31.7 mmol) in THF (200 mL) was cooled to -78° C. under an N2 atmosphere. A solution of n-butyllithium in hexane (12.3 mL, 2.58M) was added via syringe and the mixture stirred for 10 min at -78° C. and 15 min at 0° C. The mixture was cooled to -78° C. and product from Step B (5.3 g, 14.4 mmol) in THF (50 mL) was added dropwise. The reaction was stirred for 30 min and then methyl iodide (0.94 mL, 15.1 mmol) was added. The reaction was allowed to warm to room temperature overnight, and then quenched with water and 10% aqueous NaOH for 1 h. The DMF was removed in vacuo and water added. The aqueous solution was acidified with 6N HCl and extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over MgSO4. The solution was filtered and the filtrate freed of solvent to give the title compound (6.25 g, crude product). 1H NMR (300 MHz,DMSO-d6) 1.20(s,9H), 1.70(s,3H), 3.17(d,1H), 3.80(d,1H), 7.60(s,1H), 8.20(s,1H,exch.).

Workup

  1. temperatureThe mixture was cooled to -78° C.
  2. stirringThe reaction was stirred for 30 min
  3. temperatureto warm to room temperature overnight
  4. customquenched with water and 10% aqueous NaOH for 1 h
  5. customThe DMF was removed in vacuo and water
  6. additionadded
  7. extractionextracted with ethyl acetate
  8. washThe organic phase was washed with saturated brine
  9. dry with materialdried over MgSO4
  10. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-2375617547cc4c73a1bc87bf1e639c93
Source dataset
uspto-grants-1993_06
Patent number
US05216020

Reaction notes

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