Water → HCID 69584211, compound

HRID 2119841Notes

Reaction equation

HRID 2119841 reaction equation
[OH:1][C@@H:2]([CH2:18][N:19]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[H-].[Na+].Br[CH2:34][C:35]#[N:36].O>C1COCC1>[OH:1][C@@H:2]([CH2:18][N:19]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:34][C:35]#[N:36])=[CH:26][CH:25]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11534Bromoacetonitrile2×HCID 24758Sodium hydrideHCID 54420518HCID 54420518, compound

Product 1

HCID 69584211HCID 69584211, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the phenol prepared in example 91 (608 mg, 1.5 mmol) in THF (20 mL) at 0° C. was addded sodium hydride (66 mg of a 60% dispersion in oil, 1.66 mmol). After ten minutes bromoacetonitrile (199 mg, 1.66 mmol) was added. The suspension was stirred at room temperature whereupon another portion of bromoacetonitrile (360 mg, 3 mmol) was added and stirring continued until the reaction was complete by TLC. Water (50 mL) was added to the reaction and the two layers separated. The aqueous phase was extracted with ether (2×40 mL) and the combined organic phases dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with 10% MeOH/CHCl3 to provide 350 mg (53%) of product. Anal. Calcd for C27H30N3O3: C, 67.56; H 6.30; N, 8.75. Found: C, 67.39; H, 6.51; N. 8.49.

Workup

  1. customat 0° C.
  2. additionwas added
  3. customthe two layers separated
  4. extractionThe aqueous phase was extracted with ether (2×40 mL)
  5. dry with materialthe combined organic phases dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. washeluting with 10% MeOH/CHCl3

Sources & evidence

ORD record
ord-548b6eaf9c024cd189a2c0c1ad620588
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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