Water → HCID 66820080, compound

HRID 1044750Notes

Reaction equation

HRID 1044750 reaction equation
[N:1]([CH2:4][C:5]1[S:9][C:8]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)=[N:7][CH:6]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[CH3:15][C:10]1([C:8]2[S:9][C:5]([CH2:4][NH2:1])=[CH:6][N:7]=2)[O:14][CH2:13][CH2:12][O:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 91452403HCID 91452403, compound

Product 1

HCID 66820080HCID 66820080, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the crude azide (113 mg, 0.50 mmol) in THF (6 mL) were added polymer supported Ph3P (262 mg, 1.00 mmol) and water (2 mL). The reaction mixture was stirred at 60° C. for 1 h, cooled down to rt, filtered and concentrated under reduced pressure. The residue was redissolved in CH2Cl2/MeOH 9:1, dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as an orange oil. LC-MS-conditions 02: tR=0.48 min.

Workup

  1. temperaturecooled down to rt
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was redissolved in CH2Cl2/MeOH 9:1
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1caf75cf754944bca4cd3f5b281f5735
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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