Potassium Carbonate → HCID 86627028, compound

HRID 1963661Notes

Reaction equation

HRID 1963661 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])=[CH:25][CH:24]=2)[C:20]([OH:38])=[CH:19][CH:18]=1>CN(C=O)C>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:38][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])=[C:21]([C:23]2[CH:24]=[CH:25][C:26]([S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])=[CH:27][CH:28]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 67240920HCID 67240920, compound

Product 1

HCID 86627028HCID 86627028, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flask was charged with tert-butylbromoacetate (0.42 ml), dry DMF (20 ml), potassium carbonate (0.36 g) and the product from example 1 step (ii) (0.9 g) and then stirred at room temperature overnight. The mixture was quenched in water and extracted with diethylether, dried (MgSO4) and concentrated under reduced pressure to give an oil. The oil was purified by chromatography on silica eluting with isohexane/diethylether 2:1 to give the sub-title compound as a colourless oil, yield 0.6 g.

Workup

  1. customThe mixture was quenched in water
  2. extractionextracted with diethylether
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil
  6. customThe oil was purified by chromatography on silica eluting with isohexane/diethylether 2:1

Sources & evidence

ORD record
ord-d9bbf9fb5026401ca484c31cd7d8c4e4
Source dataset
uspto-grants-2013_04
Patent number
US08415394B2

Reaction notes

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