Potassium Carbonate → HCID 59708791, compound

HRID 1097294Notes

Reaction equation

HRID 1097294 reaction equation
Cl.Cl.[N:3]1([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:24](=O)([O-])[O-].[K+].[K+].I[CH:31]([CH2:35][CH3:36])[C:32]([O-:34])=[O:33]>CC(C)=O>[CH3:24][O:34][C:32](=[O:33])[CH2:31][CH2:35][CH2:36][N:6]1[CH2:7][CH2:8][N:3]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17852349HCID 17852349, compoundHCID 66811254HCID 66811254, compound

Product 1

HCID 59708791HCID 59708791, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 10 (3.30 g, 9.30 mmol) was added slowly to a stirred suspension of potassium carbonate (4.10 g, 29.7 mmol) in acetone (120 mL). After 0.5 hour, iodobutyrate (4.0 mL, 29.60 mmol) was added and the reaction was stirred at reflux for 14 hours. The reaction mixture was concentrated to dryness and the residue was taken up in water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic extracts were successively washed with water and brine, dried over anhydrous sodium sulfate and concentrated to an oil. Purification by column chromatography (silica gel, dichloromethane, then 95:5 dichloromethane/methanol, v/v) gave 11 (3.27 g, 91%) as an orange oil: 1H NMR (500 MHz, CDCl3) δ 1.62-1.71 (m, 4H), 3.11-3.17 (m, 5H), 2.39-3.41 (m, 2H), 3.48-3.77 (m, 4H), 7.83-7.91 (m, 4H), 9.33 (br, 2H), 11.54 (br, 1H); ESI MS m/z 288 [C16H21N3O2+H]+.

Workup

  1. temperatureat reflux for 14 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. extractionextracted with dichloromethane (3×50 mL)
  4. washThe combined organic extracts were successively washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to an oil
  7. customPurification by column chromatography (silica gel, dichloromethane

Sources & evidence

ORD record
ord-98465963a3d94eeabd79440f6f183a7a
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

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