Triphenylphosphine → HCID 11521972, compound

HRID 229839Notes

Reaction equation

HRID 229839 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28]([N:30]1[CH2:36][C@@H:35]([OH:37])[C@H:34]([N:38]=[N+]=[N-])[CH2:33][CH2:32][C@H:31]1[CH3:41])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.O.C1(C)C=CC=CC=1>[CH2:20]([O:27][C:28]([N:30]1[CH2:36][C@@H:35]([OH:37])[C@H:34]([NH2:38])[CH2:33][CH2:32][C@H:31]1[CH3:41])=[O:29])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 11688077HCID 11688077, compound

Product 1

HCID 11521972HCID 11521972, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Triphenylphosphine (2.13 g, 8.14 mmol) was added to a solution (2R,5R,6R)-5-Azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (1.65 g, 5.43 mmol) in THF (200 ml) and H2O (0.8 ml), then was heated to 45 degrees C. overnight. The reaction mixture was then diluted with toluene (100 ml×2) and was azeotroped in vacuo by rotary evaporation twice. The resulting oil was dissolved in MeOH and HCl in Et2O and the resulting salt was collected following filtration and was used in the next reaction without further purification (1.7 g, quantitative).

Workup

  1. customovernight
  2. customwas azeotroped in vacuo by rotary evaporation twice
  3. dissolutionThe resulting oil was dissolved in MeOH
  4. customHCl in Et2O and the resulting salt was collected
  5. filtrationfiltration
  6. customwas used in the next reaction without further purification (1.7 g, quantitative)

Sources & evidence

ORD record
ord-16f66d5a4eab490e973f5c530f3bfef4
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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