Triphenylphosphine → 3-[2-(N-allyloxycarbonyl-N-aminosulfonylamino)ethyl]imidazo[5,1-b]thiazole

HRID 1603444Notes

Reaction equation

HRID 1603444 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH2:14][CH2:15][C:16]1[N:17]2[CH:23]=[N:22][CH:21]=[C:18]2[S:19][CH:20]=1.[CH2:24]([O:27][C:28]([NH:30][S:31]([NH2:34])(=[O:33])=[O:32])=[O:29])[CH:25]=[CH2:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.O1CCCC1>[CH2:24]([O:27][C:28]([N:30]([CH2:14][CH2:15][C:16]1[N:17]2[CH:23]=[N:22][CH:21]=[C:18]2[S:19][CH:20]=1)[S:31]([NH2:34])(=[O:33])=[O:32])=[O:29])[CH:25]=[CH2:26]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19605053Allyl sulfamoylcarbamateHCID 196050553-(2-Hydroxyethyl)imidazo[5,1-b]thiazole

Product 1

HCID 196050763-[2-(N-allyloxycarbonyl-N-aminosulfonylamino)ethyl]imidazo[5,1-b]thiazoleYield 50.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere at -38° C., 0.77 ml of diethyl azodicarboxylate was added dropwise to 10 ml of an anhydrous tetrahydrofuran solution containing 550 mg of 3-(2-hydroxyethyl)imidazo[5,1-b]thiazole, 884 mg of N-allyloxycarbonyl-N-aminosulfonylamine and 1286 mg of triphenylphosphine, and the mixture was then stirred at -38° C. to -32° C. for 30 minutes and further stirred for 10 minutes while the solution was heated up to 0° C. The solvent was evaporated under reduced pressure to obtain an oil, and this oil was then dissolved in 50 ml of dichloromethane. Further, extraction was carried out with 2N hydrochloric acid (20 ml×2), and the combined aqueous layer was then washed with 10 ml of dichloromethane. Afterward, the solution was adjusted to pH 9 with anhydrous potassium carbonate, and then subjected to extraction with dichloromethane (30 ml×2). The dichloromethane extract was dried (anhydrous magnesium sulfate:anhydrous potassium carbonate=1:1) and then filtered, and the solvent was evaporated under reduced pressure. Afterward, the resulting oil was purified by a silica gel column chromatograph to obtain 548 mg of the title compound as a milky white amorphous.

Workup

  1. stirringfurther stirred for 10 minutes while the solution
  2. customThe solvent was evaporated under reduced pressure
  3. customto obtain an oil
  4. extractionFurther, extraction
  5. washthe combined aqueous layer was then washed with 10 ml of dichloromethane
  6. extractionsubjected to extraction with dichloromethane (30 ml×2)
  7. extractionThe dichloromethane extract
  8. dry with materialwas dried (anhydrous magnesium sulfate:anhydrous potassium carbonate=1:1)
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure
  11. customAfterward, the resulting oil was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-3ad919ce85f148b883799f2d9b81f5ae
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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