Triphenylphosphine → HCID 70196109, compound

HRID 456264Notes

Reaction equation

HRID 456264 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C@H:7]1[C@H:11]([N:12]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[S:13]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][N:9]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:8]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1COCC1.O>[NH2:1][CH2:4][CH2:5][CH2:6][C@H:7]1[C@H:11]([N:12]([CH2:25][CH2:26][CH:27]([CH3:28])[CH3:29])[S:13]([C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH2:10][N:9]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH2:8]1

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 86666334HCID 86666334, compound

Product 1

HCID 70196109HCID 70196109, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (3R*,4S*)-3-(3-azidopropyl)-4-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}pyrrolidine-1-carboxylate (0.55 g, 1.05 mmol) in toluene (50 mL), PPh3 (0.28 g, 1.05 mmol) was added and the mixture was heated at reflux for 1.5 hours. The mixture was diluted with 10 mL THF, H2O was added (28 mg, 1.57 mmol) and the reaction was heated at reflux for additional 1.5 hours. The solvents were evaporated and the residue was purified by column chromatography on silica gel eluting with 5→10% MeOH in CH2Cl2 giving the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. additionwas added (28 mg, 1.57 mmol)
  4. temperaturethe reaction was heated
  5. temperatureat reflux for additional 1.5 hours
  6. customThe solvents were evaporated
  7. customthe residue was purified by column chromatography on silica gel eluting with 5→10% MeOH in CH2Cl2 giving the title compound

Sources & evidence

ORD record
ord-4c4c49c3b82f453fa429e95f854a585f
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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