Water → HCID 59073689, compound

HRID 1044730Notes

Reaction equation

HRID 1044730 reaction equation
[N:1]([CH2:4][C:5]1[O:9][C:8]([C:10](=[O:12])[CH3:11])=[CH:7][CH:6]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[O:9][C:8]([C:10](=[O:12])[CH3:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 59073804HCID 59073804, compound

Product 1

HCID 59073689HCID 59073689, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the crude azide (500 mg, 3.03 mmol) in THF (15 mL) were added Ph3P (polymer-supported, 3.0 mmol/g, 1.5 eq.) and water (5 mL). The reaction mixture was stirred at 60° C. until reaction completion, cooled down to rt and filtered. Sat. aq. NaHCO3 and EA were then added, the layers separated and the aq. layer extracted with EA (1×). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by FC (9:1 CH2Cl2/MeOH) and the title compound was obtained as an orange oil. LC-MS-conditions 02: tR=0.27 min; [M+AcCN+H]+=181.61.

Workup

  1. temperaturecooled down to rt
  2. filtrationfiltered
  3. additionSat. aq. NaHCO3 and EA were then added
  4. customthe layers separated
  5. extractionthe aq. layer extracted with EA (1×)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue was purified by FC (9:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-945379cb4b884cc691a99278c2e6bc4e
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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