Triphenylphosphine → HCID 19605084, compound

HRID 1603442Notes

Reaction equation

HRID 1603442 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH2:14][C:15]1[N:16]2[CH:22]=[N:21][CH:20]=[C:17]2[S:18][CH:19]=1.[CH2:23]([O:26][C:27]([N-:29][S:30]([NH2:33])(=[O:32])=[O:31])=[O:28])[CH:24]=[CH2:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.O1CCCC1>[CH2:23]([O:26][C:27]([N:29]([CH2:14][C:15]1[N:16]2[CH:22]=[N:21][CH:20]=[C:17]2[S:18][CH:19]=1)[S:30]([NH2:33])(=[O:32])=[O:31])=[O:28])[CH:24]=[CH2:25]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15428311HCID 15428311, compoundHCID 178459890HCID 178459890, compound

Product 1

HCID 19605084HCID 19605084, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere at -51° C., 0.71 ml of diethyl azodicarboxylate was added dropwise to 5 ml of an anhydrous tetrahydrofuran solution containing 463 mg of 3-hydroxymethylimidazo[5,1-b]thiazole, 811 mg of N-allyloxycarbonyl-N-aminosulfonylamide and 1180 mg of triphenylphosphine, and the mixture was then stirred at -51° C. to -37° C. for 15 minutes and further stirred for 70 minutes, while the solution was heated up to room temperature. The solvent was evaporated under reduced pressure to obtain an oil, and this oil was then dissolved in 50 ml of ethyl acetate. Further, the solution was extracted with 2N hydrochloric acid (30 ml×2), and the combined aqueous layer was then washed with 20 ml of ethyl acetate. After neutralized (pH 7) with sodium hydrogencarbonate, the neutralized solution was extracted with ethyl acetate (100 ml×2). The thus extracted organic layer was dried over anhydrous magnesium sulfate and then filtered, and the solvent was evaporated under reduced pressure. Afterward, the resulting oil was purified by a silica gel column chromatograph and successively Cephadex LH-20 to obtain 145.6 mg of the title compound in a milky white amorphous state.

Workup

  1. stirringfurther stirred for 70 minutes, while the solution
  2. customThe solvent was evaporated under reduced pressure
  3. customto obtain an oil
  4. extractionFurther, the solution was extracted with 2N hydrochloric acid (30 ml×2)
  5. washthe combined aqueous layer was then washed with 20 ml of ethyl acetate
  6. extractionthe neutralized solution was extracted with ethyl acetate (100 ml×2)
  7. dry with materialThe thus extracted organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure
  10. customAfterward, the resulting oil was purified by a silica gel column chromatograph and successively Cephadex LH-20

Sources & evidence

ORD record
ord-52899fe1d5674109bb7269615c75defb
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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