Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 117689120 | HCID 117689120 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 123633873 | HCID 123633873 | — |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365515B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-793f3c8794b14572a48452ff950c4441 |
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| Source note | uspto-grants-2016_06 |
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