Isopropyl iodide → HCID 66971949, compound

HRID 1364195Notes

Reaction equation

HRID 1364195 reaction equation
[C:1]([NH:20][C@@H:21]1[CH2:27][CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[NH:23][C:22]1=[O:32])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH:36]([CH3:38])[CH3:37]>CN(C)C=O>[CH:36]([N:23]1[C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[CH2:26][CH2:27][C@@H:21]([NH:20][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:22]1=[O:32])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 66971957HCID 66971957, compound

Product 1

HCID 66971949HCID 66971949, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 35 mL heavy-walled sealable tube was fitted with a stirbar and septa. The tritylated benzolactam from Step 4 (2.02 g, 4.83 mmol) and N,N-dimethylformamide (20 mL) were added, giving a solution that was cooled to 0° C. Sodium hydride (1.08 g, 60%/oil, 27.0 mmol) was added cautiously, giving a mixture that was stirred 5 minutes at 0° C., then removed from the cold bath and allowed to warm to room temperature. After 30 minutes, 2-iodopropane (1.0 mL, 10.0 mmol) was added, and the resulting mixture was stirred at room temperature for 18 hours. The rubber septa was then removed, the reaction vessel was sealed with a plastic screwcap, placed in an oil bath and warmed to 60° C. After 4 hours, the reaction was cooled to room temperature, diluted with H2O (100 mL) and extracted three times with diethyl ether (100 mL, then 2×50 mL). The organic extracts were combined, washed with saturated aqueous NaCl solution (50 mL), dried over MgSO4, filtered and concentrated in vacuo. The resulting oil was purified via flash chromatography on silica gel (0% to 25% ethyl acetate/hexanes linear gradient) to give the desired product.

Workup

  1. customA 35 mL heavy-walled sealable tube was fitted with a stirbar and septa
  2. customgiving a solution that
  3. customgiving a mixture that
  4. customremoved from the cold bath
  5. temperatureto warm to room temperature
  6. waitAfter 30 minutes
  7. stirringthe resulting mixture was stirred at room temperature for 18 hours
  8. customThe rubber septa was then removed
  9. customthe reaction vessel was sealed with a plastic screwcap
  10. customplaced in an oil bath
  11. temperaturewarmed to 60° C
  12. waitAfter 4 hours
  13. temperaturethe reaction was cooled to room temperature
  14. additiondiluted with H2O (100 mL)
  15. extractionextracted three times with diethyl ether (100 mL
  16. washwashed with saturated aqueous NaCl solution (50 mL)
  17. dry with materialdried over MgSO4
  18. filtrationfiltered
  19. concentrationconcentrated in vacuo
  20. customThe resulting oil was purified via flash chromatography on silica gel (0% to 25% ethyl acetate/hexanes linear gradient)

Sources & evidence

ORD record
ord-90547b8145054225a4f6752ec2332307
Source dataset
uspto-grants-2011_02
Patent number
US07888345B2

Reaction notes

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