Water → HCID 66820044, compound

HRID 1044757Notes

Reaction equation

HRID 1044757 reaction equation
[N:1]([CH2:4][C:5]1[S:6][C:7]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)=[CH:8][N:9]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[CH3:15][C:10]1([C:7]2[S:6][C:5]([CH2:4][NH2:1])=[N:9][CH:8]=2)[O:14][CH2:13][CH2:12][O:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 91233241HCID 91233241, compound

Product 1

HCID 66820044HCID 66820044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the crude azide (565 mg, 2.50 mmol) in THF (12 mL) were added polymer-supported Ph3P (2.0 eq.) and water (4 mL). The reaction mixture was stirred at 60° C. until completion of the reaction, cooled down to rt, filtered and partitioned between EA and sat. aq. NaHCO3. The layers were separated and the aq. layer extracted with EA. The combined org. extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a brown oil after purification by FC (CH2Cl2-MeOH 1:0 to 9:1). LC-MS-conditions 01: tR=0.38 min; [M+H]+=200.96.

Workup

  1. temperaturecooled down to rt
  2. filtrationfiltered
  3. custompartitioned between EA and sat. aq. NaHCO3
  4. customThe layers were separated
  5. extractionthe aq. layer extracted with EA
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b62c72f7811948ad9db581cd9c16fbb4
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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