Water → HCID 56680440, compound

HRID 2243204Notes

Reaction equation

HRID 2243204 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:6][NH:5][C:4](=[O:7])[CH:3]1[O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:32]([O:34][C:35](=[O:38])[CH2:36]Br)[CH3:33].O>C1COCC1>[CH2:32]([O:34][C:35](=[O:38])[CH2:36][N:5]1[CH2:6][C:2]([CH3:21])([CH3:1])[CH:3]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:18])([F:20])[F:19])[CH:10]=2)[C:4]1=[O:7])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 56670277HCID 56670277, compound2×

Product 1

HCID 56680440HCID 56680440, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. stirring solution of 4-(4,4-Dimethyl-2-oxo-pyrrolidin-3-yloxy)-2-trifluoromethyl-benzonitrile (Compound (1), product of Example 3, Step E, 5.00 g, 16.8 mmoles) in 100 mL THF under a nitrogen atmosphere was added lithium bis(trimethylsilyl)amide (1M in THF, 18.4 mL, 18.4 mmoles) and bromoacetic acid ethyl ester (2) (2.0 mL, 18.4 mmoles). The cooling bath was allowed to warm up to ambient temperature overnight. Water (25 mL) was added and the reaction mixture was concentrated in vacuo. Methylene chloride (100 mL) and water (50 mL) was added, the mixture is agitated and the layers are separated. The organic layer was concentrated in vacuo. The product (3) is used as is for the next reaction.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionMethylene chloride (100 mL) and water (50 mL) was added
  3. customthe layers are separated
  4. concentrationThe organic layer was concentrated in vacuo
  5. customas is for the next reaction

Sources & evidence

ORD record
ord-e44fb8c9e8d24dd49b3b8600ccc52afc
Source dataset
uspto-grants-2010_03
Patent number
US07674819B2

Reaction notes

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