Triphenylphosphine → HCID 22036655, compound

HRID 229786Notes

Reaction equation

HRID 229786 reaction equation
[N:1]([CH:4]1[CH2:10][CH:9]([CH3:11])[CH2:8][N:7]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)(=[O:14])=[O:13])[CH2:6][CH:5]1[OH:21])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][CH:4]1[CH2:10][CH:9]([CH3:11])[CH2:8][N:7]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)(=[O:14])=[O:13])[CH2:6][CH:5]1[OH:21]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 22036689HCID 22036689, compound

Product 1

HCID 22036655HCID 22036655, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

4-Azido-6-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol (0.33 g, 1.06 mmol) was dissolved in THF (50 ml) and H2O (0.2 ml). PPh3 (0.42 g, 1.59 mmol) was added to this solution. The reaction mixture was stirred at 45° C. over night. TLC showed no starting material left. THF was evaperated, azeotroped by toluene (2×100 ml). The resulting thick oil was dissolved in MeOH, treated with HCl in ether to adjust pH to acidic. More ether was added and the solution turned cloudy to give the title compound as a white precipitate (0.21 g, 71% yield) MS (M+H+) 286.0; 1H-NMR (400 Hz, CD3OD): d (ppm): 8.72(d, 1H), 8.14-7.99(m, 2H), 7.68(m, 1H), 3.85-3.69(m, 2H), 3.38-3.22(m, 3H), 3.10-3.04(m, 2H), 2.04(m, 1H), 1.82-1.66(m, 2H), 1.02(d, 3H)

Workup

  1. waitleft
  2. customazeotroped by toluene (2×100 ml)
  3. dissolutionThe resulting thick oil was dissolved in MeOH
  4. additiontreated with HCl in ether
  5. additionMore ether was added

Sources & evidence

ORD record
ord-0c52c582d00b4054a4a0946433ab0768
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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