Tetrahydrofuran → HCID 23155408, compound

HRID 2080808Notes

Reaction equation

HRID 2080808 reaction equation
C1COCC1.[CH2:6]([N:9]([CH2:32][CH2:33][CH3:34])[CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH2:23][NH:24][CH2:25][C:26]3[NH:27][CH:28]=[CH:29][N:30]=3)[CH:20]=2)[C:15]1=O)[CH2:7][CH3:8]>CO>[NH:27]1[CH:28]=[CH:29][N:30]=[C:26]1[CH2:25][NH:24][CH2:23][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([CH2:13][CH2:12][CH2:11][CH2:10][N:9]([CH2:6][CH2:7][CH3:8])[CH2:32][CH2:33][CH3:34])[CH2:22]2

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 23155361HCID 23155361, compound

Product 1

HCID 23155408HCID 23155408, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A THF solution (2.0 ml) containing the compound (24.3 mg) obtained in Example 7-7 was added with a 1 mol/l borane-THF complex/THF solution (0.41 ml). The whole was refluxed under heating for 16 hours. After having been cooled to 0° C., the solution was added with methanol to stop the reaction and concentrated. The residue was added with a 1 mol/l hydrochloric acid (4.0 ml) and the whole was refluxed under heating for 3 hours. After having been left standing for cooling, the resultant was added with a 1 mol/l sodium hydroxide aqueous solution (5 ml) and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried with anhydrous sodium sulfate. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (12.5 mg) as a colorless oily substance.

Workup

  1. temperatureThe whole was refluxed
  2. temperatureunder heating for 16 hours
  3. customthe reaction
  4. concentrationconcentrated
  5. additionThe residue was added with a 1 mol/l hydrochloric acid (4.0 ml)
  6. temperaturethe whole was refluxed
  7. temperatureunder heating for 3 hours
  8. waitAfter having been left
  9. temperaturefor cooling
  10. additionthe resultant was added with a 1 mol/l sodium hydroxide aqueous solution (5 ml)
  11. extractionthe whole was subjected to extraction with chloroform
  12. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  13. dry with materialdried with anhydrous sodium sulfate
  14. customThe residue obtained
  15. distillationby distilling the solvent
  16. customoff was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-c8bddc0ba7ec44679cbae792d0cd7ad0
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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