N-bromobutanimide → HCID 66726147, compound

HRID 2364946Notes

Reaction equation

HRID 2364946 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])[CH2:3][CH2:2]1.[Br:15]N1C(=O)CCC1=O>CN(C=O)C>[Br:15][C:11]1[CH:12]=[CH:13][C:8]([NH:7][CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[C:9]([OH:14])[CH:10]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66726405HCID 66726405, compound

Product 1

HCID 66726147HCID 66726147, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of intermediate D7 (0.66 g, 3.415 mmol) and N-bromosuccinimide (0.669 g, 3.757 mmol) in DMF (10 ml) was stirred at r.t. for 1 h. Subsequently, the r.m. was washed with an aqueous saturated NaHCO3 solution. The organic layer was separated, dried (Na2SO4), filtered and the solvent 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 D9 (0.433 g, 46.6%) as a reddish solid.

Workup

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

Sources & evidence

ORD record
ord-af465b0c41774b84b0bace53ee4fd423
Source dataset
uspto-grants-2014_04
Patent number
US08697689B2

Reaction notes

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