N-bromobutanimide → HCID 66726429, compound

HRID 2361748Notes

Reaction equation

HRID 2361748 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[Br:19]N1C(=O)CCC1=O>CN(C=O)C>[Br:19][C:15]1[CH:16]=[CH:17][C:12]([NH:11][CH:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)=[C:13]([OH:18])[CH:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66726640HCID 66726640, compound

Product 1

HCID 66726429HCID 66726429, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of intermediate D19 (1 g, 4.011 mmol) and N-bromosuccinimide (0.785 g, 4.412 mmol) in DMF (15 ml) was stirred at room temperature for 1 h. Subsequently, the reaction mixture was washed with NaHCO3 (aqueous sat. solution). The organic layer was separated, dried (Na2SO4), and the solvent was evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/EtOAc 8:2 as eluent): The desired fractions were collected and evaporated in vacuo to yield D22 (0.433 g, 32.89%) as a reddish solid.

Workup

  1. washSubsequently, the reaction mixture was washed with NaHCO3 (aqueous sat. solution)
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was evaporated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel; DCM/EtOAc 8:2 as eluent)
  6. customThe desired fractions were collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f48623715dd64096b508aa42945199df
Source dataset
uspto-grants-2014_04
Patent number
US08691813B2

Reaction notes

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