Potassium Carbonate → HCID 69411870, compound

HRID 1269360Notes

Reaction equation

HRID 1269360 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[CH2:22][O:23][C:24]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][N+:33]([O-:35])=[O:34])=[O:25])=[C:12](\[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)/[C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br-].Br[CH2:38][CH2:39][NH+:40]([CH2:43][CH3:44])[CH2:41][CH3:42].C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-:52]>CN(C=O)C>[Cl-:52].[CH2:39]([NH+:40]([CH2:43][CH3:44])[CH2:41][CH2:42][O:14][C:13](=[O:15])/[C:12](/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:11](/[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=1)\[CH2:22][O:23][C:24]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][N+:33]([O-:35])=[O:34])=[O:25])[CH3:38]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 154368581069-72-3HCID 18448155HCID 18448155, compound

Product 1

HCID 69411870HCID 69411870, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2Z)-3-[4-(methylsulfonyl)phenyl]-4-[({[5-(nitrooxy)pentyl]oxy}carbonyl)oxy]-2-phenylbut-2-enoic acid (1 eq, 0.2M) in DMF was added 2-bromo-N,N-diethylethanaminium bromide (1 eq) and K2CO3 (2 eq). The reaction was stirred at rt for 12 h and saturated aqueous NH4Cl was added. The mixture was extracted with EtOAc and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel eluted with 100% EtOAc and concentrated. The neutral amine was dissolved in Et2O and an excess of 2M HCl in Et2O was added. The mixture was stirred for 2 h and concentrated. The residue was dissolved in water and freeze dried to give the titled compound. 1H NMR (acetone-d6, 500 M Hz): δ 7.76 (d, 2H), 7.44 (d, 2H), 7.21–7.13 (m, 5H), 5.41 (s, 2H), 4.78–4.74 (m, 2H), 4.53 (t, 2H), 4.08 (t, 2H), 3.44–3.40 (m, 2H), 3.04 (s, 3H), 3.04–3.0 (m, 4H), 1.76–1.71 (m, 2H), 1.65–1.60 (m, 2H), 1.45–1.40 (m, 2H), 1.22 (t, 6H).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluted with 100% EtOAc
  8. concentrationconcentrated
  9. dissolutionThe neutral amine was dissolved in Et2O
  10. additionan excess of 2M HCl in Et2O was added
  11. stirringThe mixture was stirred for 2 h
  12. concentrationconcentrated
  13. dissolutionThe residue was dissolved in water
  14. customfreeze dried

Sources & evidence

ORD record
ord-1075fb63c741461582349e6e8486d6c9
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

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