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Potassium Carbonate → HCID 69411870、化合物

HRID 1269360
ノート
印刷プレビュー

反応式

HRID 1269360 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 154368582-Bromoethyl(diethyl)azanium;bromideHCID 18448155HCID 18448155、化合物

生成物 1

HCID 69411870HCID 69411870、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1075fb63c741461582349e6e8486d6c9
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07199154B2

反応ノート

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