Dimethylformamide → HCID 69585139, compound

HRID 1243157Notes

Reaction equation

HRID 1243157 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:15][C:16]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].CN(C)C=O.[H-].[Na+].I[CH2:31][CH3:32]>O>[CH3:1][O:2][C:3]([C:5]1([N:15]([CH2:31][CH3:32])[C:16]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 69585373HCID 69585373, compound

Product 1

HCID 69585139HCID 69585139, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cooled solution of ester from Example 53D (101 mg, 0.33 mmol) and anhydrous N,N-dimethylforamide (1.5 mL) under N2 was added 60% dispersion sodium hydride (35 mg, 0.825 mmol) and then stirred for 15 minutes. Iodoethane (40 μL, 0.495 mmol) was added. The reaction was stirred at room temperature for 18 hours, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column (20% ethyl acetate/hexane) to provide the titled compound as a clear, colorless syrup (51 mg, 46%). 1H NMR (δ, CDCl3): 7.07–7.15 (m, 4H), 3.90 (dd, 2H), 3.71 (s, 3H), 3.35–3.5 (m, 2H), 3.00–3.08 (m, 2H), 7.75–2.8 (m, 2H), 2.55–2.6 (m, 1H), 2.19–2.3 (m 1H), 1.88–2.0 (m, 1H), 1.14 (t, 3H), 0.95 (d, 6H). MS (DCI/NH3): 334.2 (M+1).

Workup

  1. stirringThe reaction was stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel column (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c972ced4ed5f4034adadae9d20c66eb0
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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