Water → HCID 123633873, compound

HRID 2203249Notes

Reaction equation

HRID 2203249 reaction equation
[CH2:1]([O:3][C:4](=[O:67])[CH2:5][CH2:6][C:7]([C:10]1[CH:11]=[C:12]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])[C:18]1[C:13]2=[CH:14][C:15]([C:35](=[O:66])[C:36]2[CH:41]=[CH:40][C:39]([N:42]3[C:54]4[CH:53]=[CH:52][C:51]([C:55](=[N:64][OH:65])[CH2:56][CH2:57][C:58]([O:60][CH2:61][CH2:62][CH3:63])=[O:59])=[CH:50][C:49]=4[C:48]4[C:43]3=[CH:44][CH:45]=[CH:46][CH:47]=4)=[CH:38][CH:37]=2)=[C:16]2[CH:34]=[CH:33][CH:32]=[CH:31][C:17]2=1)=[N:8][OH:9])[CH3:2].C(N([CH2:73][CH3:74])CC)C.[C:75](Cl)(=[O:77])[CH3:76].[OH2:79]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:67])[CH2:5][CH2:6][C:7]([C:10]1[CH:11]=[C:12]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])[C:18]1[C:13]2=[CH:14][C:15]([C:35](=[O:66])[C:36]2[CH:41]=[CH:40][C:39]([N:42]3[C:54]4[CH:53]=[CH:52][C:51]([C:55](=[N:64][O:65][C:73](=[O:79])[CH3:74])[CH2:56][CH2:57][C:58]([O:60][CH2:61][CH2:62][CH3:63])=[O:59])=[CH:50][C:49]=4[C:48]4[C:43]3=[CH:44][CH:45]=[CH:46][CH:47]=4)=[CH:38][CH:37]=2)=[C:16]2[CH:34]=[CH:33][CH:32]=[CH:31][C:17]2=1)=[N:8][O:9][C:75](=[O:77])[CH3:76])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 117689120HCID 117689120, compound

Product 1

HCID 123633873HCID 123633873, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(11-(2-ethylhexyl)-5-{4-[3-(1-hydroxyimino-3-propoxycarbonyl-propyl)-carbazole-9-yl]-benzoyl}-11H-benzo[a]carbazol-8-yl)-4-hydroxyimino-butyric acid ethyl ester (260 mg, 0.289 mmol) in tetrahydrofurane (THF) (5 mL) are added triethylamine (86 mg, 0.84 mmol) and acetyl chloride (66 mg, 0.84 mmol) at 0° C. After stirring for 1.5 hours, the reaction mixture is poured into water, and the crude product is extracted with ethyl acetate. The organic layer is washed with water and brine, dried over MgSO4. After concentration, the crude product is purified by column chromatography on silica gel eluting with ethyl acetate to obtain an off-white resin (169 mg; 60%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.84 (t), 0.91 (t), 1.19-1.54 (m), 2.28 (s), 2.31 (s), 2.60-2.69 (m), 3.27-3.35 (m), 4.09 (q), 4.14 (q), 4.73-4.85 (m), 7.36 (t), 7.49 (t), 7.56-7.78 (m), 7.85 (d), 7.89 (d), 8.20 (d), 8.22 (d), 3.23 (d), 8.49 (s), 8.53 (s), 8.60 (d), 8.67 (d).

Workup

  1. extractionthe crude product is extracted with ethyl acetate
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentration
  5. customthe crude product is purified by column chromatography on silica gel eluting with ethyl acetate
  6. customto obtain an off-white resin (169 mg; 60%)

Sources & evidence

ORD record
ord-793f3c8794b14572a48452ff950c4441
Source dataset
uspto-grants-2016_06
Patent number
US09365515B2

Reaction notes

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