HCID 21087446, compound → HCID 21087443, compound

HRID 1368078Notes

Reaction equation

HRID 1368078 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:13][C@H:14]2[CH2:18][N:17]([C@@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])[C:16](=O)[CH2:15]2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:13][C@H:14]2[CH2:15][CH2:16][N:17]([C@@H:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH3:20])[CH2:18]2)[CH2:10][CH2:11][CH2:12]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 21087446HCID 21087446, compound

Product 1

HCID 21087443HCID 21087443, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of nitrogen, 1 M borane-tetrahydrofuran complex solution (6.4 ml) was added dropwise to tetrahydrofuran solution (15 ml) of 4-(R)-[1-(tert-butoxycarbonyl)amino-1-cyclobutyl]methyl-1-[1-(R)-phenylethyl]-2pyrrolidone (isomer B2) (797 mg, 2.14 mmol) under ice-cooling, and the mixture was stirred at room temperature for 13 hours. The solvent was evaporated under a reduced pressure, and the resulting residue was mixed with 80% aqueous ethanol (15 ml) and triethylamine (3 ml) and heated under reflux for 4 hours. After cooling, the solvent was evaporated under a reduced pressure, and the thus obtained residue was mixed with chloroform (30 ml), washed with water (10 ml) and saturated sodium chloride aqueous solution (10 ml) and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel column chromatography and eluted with chloroform:methanol=20:1, thereby obtaining 743 mg (97%) of the title compound as colorless oil.

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated under a reduced pressure
  3. additionthe resulting residue was mixed with 80% aqueous ethanol (15 ml) and triethylamine (3 ml)
  4. temperatureheated
  5. temperatureunder reflux for 4 hours
  6. temperatureAfter cooling
  7. customthe solvent was evaporated under a reduced pressure
  8. additionthe thus obtained residue was mixed with chloroform (30 ml)
  9. washwashed with water (10 ml) and saturated sodium chloride aqueous solution (10 ml)
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated under a reduced pressure
  12. washeluted with chloroform

Sources & evidence

ORD record
ord-11f2c51b419b4731b9c527cfc7c5488d
Source dataset
uspto-grants-2003_06
Patent number
US06573260B1

Reaction notes

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