Hydrochloric Acid → HCID 57517488, compound

HRID 2368090Notes

Reaction equation

HRID 2368090 reaction equation
[N:1]([CH:4]([CH3:24])[CH2:5][O:6][CH:7]1[CH2:10][N:9]([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.C1C[O:48][CH2:47][CH2:46]1.O>>[C:12]1([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]2[CH2:10][CH:7]([O:6][CH2:5][CH:4]([NH:1][C:47](=[O:48])[CH3:46])[CH3:24])[CH2:8]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 21881883Oxolane--water (1/1)HCID 57517487HCID 57517487, compound

Product 1

HCID 57517488HCID 57517488, compound

Conditions

Temperature
60 °C

Procedure

A solution of 3-(2-azidopropoxy)-1-(diphenylmethyl)azetidine (350 mg) and triphenylphosphine (340 mg) in THF/water (15 mL/5 mL) was heated under reflux for 2 hr. The mixture was allowed to cool, 1M hydrochloric acid was added thereto, and the mixture was washed with diethyl ether. The obtained aqueous solution was neutralized with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (15 mL), acetic anhydride (1 mL) was added thereto, and the mixture was stirred at 60° C. for 5 hr. The mixture was allowed to cool, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (0.31 g).

Workup

  1. temperatureunder reflux for 2 hr
  2. temperatureto cool
  3. washthe mixture was washed with diethyl ether
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate (15 mL)
  8. additionacetic anhydride (1 mL) was added
  9. temperatureto cool
  10. washwashed with water and saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1766e566a6154ade897845d96b2bb02d
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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