N-bromobutanimide → HCID 66726429, compound

HRID 2364947Notes

Reaction equation

HRID 2364947 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 D8 (1 g, 4.011 mmol) and N-bromosuccinimide (0.785 g, 4.412 mmol) in DMF (15 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 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 D10 (0.433 g, 32.89%) 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 was 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-295b343a95c5406993226fe60c276a44
Source dataset
uspto-grants-2014_04
Patent number
US08697689B2

Reaction notes

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