HCID 20741423, compound → HCID 20741403, compound

HRID 457405Notes

Reaction equation

HRID 457405 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C@H:16]1[CH2:20][N:19]([C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[C:18](=O)[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C@@H:16]1[CH2:17][CH2:18][N:19]([C@@H:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH3:22])[CH2:20]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 20741423HCID 20741423, compound

Product 1

HCID 20741403HCID 20741403, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of nitrogen 1Mborane-tetrahydrofuran complex (4.6 ml) was added dropwise to tetrahydrofuran (10 ml) solution of 4-(R)-[1-tert-butoxycarbonylamino-1-phenylmethyl]-1-[1-(R)-phenylethyl]-2-pyrrolidone [F1] (600 mg, 1.52 mmol) under ice-cooling, and then the mixture was stirred at room temperature for 13 hours. After evaporation of the solvent under a reduced pressure, the resulting residue was mixed with 80% hydrous ethanol (15 ml) and triethylamine (3 ml) and heated under reflux for 5 hours. After spontaneous cooling, the solvent was evaporated under a reduced pressure, and chloroform (30 ml) was added to the resulting residue. This was washed with water (10 ml) and saturated brine (10 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:methanol (20:1), 510 mg (88%) of the title compound was obtained as colorless crystals.

Workup

  1. temperaturecooling
  2. customAfter evaporation of the solvent under a reduced pressure
  3. additionthe resulting residue was mixed with 80% hydrous ethanol (15 ml) and triethylamine (3 ml)
  4. temperatureheated
  5. temperatureunder reflux for 5 hours
  6. customAfter spontaneous cooling, the solvent was evaporated under a reduced pressure, and chloroform (30 ml)
  7. additionwas added to the resulting residue
  8. washThis was washed with water (10 ml) and saturated brine (10 ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under a reduced pressure
  11. washBy eluting with chloroform:methanol (20:1)

Sources & evidence

ORD record
ord-de9c642cb2da4093bd7630750387c758
Source dataset
uspto-grants-2007_03
Patent number
US07186843B2

Reaction notes

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