Tetrahydrofuran → HCID 18439397, compound

HRID 457407Notes

Reaction equation

HRID 457407 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C@H:15]1[CH2:19][N:18]([C@@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[C:17](=O)[CH2:16]1)[C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:29]1CCCC1>>[C:1]([O:5][C:6]([NH:8][CH:9]([C@H:15]1[CH2:16][CH2:17][N:18]([C@@H:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[C:19]1=[O:29])[C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 20741417HCID 20741417, compound

Product 1

HCID 18439397HCID 18439397, compoundYield 79%

Procedure

In an atmosphere of nitrogen, 1Mborane-tetrahydrofuran complex (14.8 ml) was added dropwise to a tetrahydrofuran solution (40 ml) of 4-(R)-[1-tert-butoxycarbonylamino-1-(2-furyl)methyl]-1-[1-(R)-phenylethyl]-2-pyrrolidone [F1] (2.03 g, 5.28 mmol) under ice-cooling, and then the mixture was stirred at room temperature for 17 hours. After evaporation of the solvent under a reduced pressure, the resulting residue was dissolved in 80% hydrous ethanol (40 ml) and heated under reflux for 1 hour in the presence of triethylamine (1 ml). After spontaneous cooling of the reaction solution, the solvent was evaporated under a reduced pressure, chloroform (100 ml) was added to the resulting residue, and then the resulting organic layer was washed with saturated ammonium chloride aqueous solution (80 ml) and saturated brine (80 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the resulting residue was applied to a silica gel column chromatography. By eluting with chloroform to chloroform:methanol (97:3), 1.54 g (79%) of the title compound was obtained as white crystals.

Workup

  1. temperaturecooling
  2. customAfter evaporation of the solvent under a reduced pressure
  3. dissolutionthe resulting residue was dissolved in 80% hydrous ethanol (40 ml)
  4. temperatureheated
  5. temperatureunder reflux for 1 hour in the presence of triethylamine (1 ml)
  6. temperatureAfter spontaneous cooling of the reaction solution
  7. customthe solvent was evaporated under a reduced pressure, chloroform (100 ml)
  8. additionwas added to the resulting residue
  9. washthe resulting organic layer was washed with saturated ammonium chloride aqueous solution (80 ml) and saturated brine (80 ml)
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated under a reduced pressure
  12. washBy eluting with chloroform to chloroform:methanol (97:3)

Sources & evidence

ORD record
ord-70abf1f104764fe5b6ecc9f0bbfb7f30
Source dataset
uspto-grants-2007_03
Patent number
US07186843B2

Reaction notes

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