Triphenylphosphine → HCID 11616105, compound

HRID 229816Notes

Reaction equation

HRID 229816 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 11638054HCID 11638054, compound

Product 1

HCID 11616105HCID 11616105, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

Triphenylphosphine (0.25 g, 0.952 mmol) was added to a solution of (2R,5S,6S)-5-azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.193 g, 0.635 mmol) in THF (10 ml) and H2O (0.04 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 (0.27 g, 90%).

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 (0.27 g, 90%)

Sources & evidence

ORD record
ord-dc6409e3e97f489d8356fa1ad93bc1a6
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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