N-bromobutanimide → HCID 66581757, compound

HRID 717742Notes

Reaction equation

HRID 717742 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:18]=[CH:17][C:16](=[O:19])[NH:15][C:14]2=[O:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:21]N1C(=O)CCC1=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:18]=[C:17]([Br:21])[C:16](=[O:19])[NH:15][C:14]2=[O:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66581572HCID 66581572, compound

Product 1

HCID 66581757HCID 66581757, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4 (0.6 g, 2.13 mmol) and N-bromosuccinimide (0.456 g, 2.56 mmol) was added DMF (15 mL) and stirred at ambient temperature for 3-4 h. The solution was partitioned between ethyl acetate (50 mL) and 10% Na2S2O3 (40 mL). Organic layer was separated, washed with brine (3×50 mL), dried (anhydrous Na2SO4) and concentrated under reduced pressure. The crude material was purified by flash chromatography over silica gel (70% ethyl acetate-dichloromethane) to give pure 5.

Workup

  1. customThe solution was partitioned between ethyl acetate (50 mL) and 10% Na2S2O3 (40 mL)
  2. customOrganic layer was separated
  3. washwashed with brine (3×50 mL)
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by flash chromatography over silica gel (70% ethyl acetate-dichloromethane)
  7. customto give pure 5

Sources & evidence

ORD record
ord-c1e02481b16348d8a365ed61b80c8e3e
Source dataset
uspto-grants-2015_11
Patent number
US09193731B2

Reaction notes

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