Water → HCID 22599534, compound

HRID 1760115Notes

Reaction equation

HRID 1760115 reaction equation
[N:1]([CH:4]1[N:10]=[C:9]([S:11][CH2:12][CH3:13])[C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][C:7]=2[N:6]([CH3:18])[C:5]1=[O:19])=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[NH2:1][CH:4]1[N:10]=[C:9]([S:11][CH2:12][CH3:13])[C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][C:7]=2[N:6]([CH3:18])[C:5]1=[O:19]

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 22599514HCID 22599514, compound

Product 1

HCID 22599534HCID 22599534, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.90 mmol of azide (see Step B above) in 13 mL of tetrahydrofuran to which had been added 1 mL of water is treated with an excess of triphenyphospine (2.8 equivalents) added in one portion as a solid. The reaction is stirred at room temperature under nitrogen cover for twenty hours and then diluted with ethyl acetate. The solution is extracted with 1N HCl three times, and the combined extracts are rendered basic by the addition of 5N NaOH. This is extracted three times with ethyl acetate and the combined extracts washed once with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo on a rotary evaporator at 20° C. The resulting oil is used immediately.

Workup

  1. additionadded in one portion as a solid
  2. extractionThe solution is extracted with 1N HCl three times
  3. additionthe combined extracts are rendered basic by the addition of 5N NaOH
  4. extractionThis is extracted three times with ethyl acetate
  5. washthe combined extracts washed once with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo on a rotary evaporator at 20° C

Sources & evidence

ORD record
ord-b67be2fbfde3476e8519cc1001a108da
Source dataset
uspto-grants-2005_01
Patent number
US06838455B2

Reaction notes

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