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

HRID 1603443Notes

Reaction equation

HRID 1603443 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH2:14][C:15]1[S:19][C:18]2=[CH:20][N:21]=[CH:22][N:17]2[C:16]=1[CH3:23].[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][C:15]1[S:19][C:18]2=[CH:20][N:21]=[CH:22][N:17]2[C:16]=1[CH3:23])[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 19605134{3-Methylimidazo[4,3-b][1,3]thiazol-2-yl}methanol

Product 1

HCID 196051242-(N-allyloxycarbonyl-N-aminosulfonylamino)methyl-3-methylimidazo[5,1-b]thiazoleYield 29.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere at -37° C., 0.51 ml of diethyl azodicarboxylate was added dropwise to 6.7 ml of an anhydrous tetrahydrofuran solution containing 365 mg of 2-hydroxymethyl-3-methylimidazo[5,1-b]thiazole, 586 mg of N-allyloxycarbonyl-N-aminosulfonylamine and 854 mg of triphenylphosphine, and the mixture was then stirred at -37° C. to -20° C. for 110 minutes. The solvent was evaporated under reduced pressure to obtain an oil, and this oil was then suspended in 50 ml of dichloromethane. Further, the suspension was extracted with 2N hydrochloric acid (15 ml×2), and the combined aqueous layer was then washed with 20 ml of dichloromethane. After alkalified with anhydrous potassium carbonate, the solution was further extracted with dichloromethane (30 ml×3). The combined organic layer was washed with a semi-saturated saline solution, 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 and successively Cephadex LH-20 to obtain 208.5 mg of the title compound as a milky white powder.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto obtain an oil
  3. extractionFurther, the suspension was extracted with 2N hydrochloric acid (15 ml×2)
  4. washthe combined aqueous layer was then washed with 20 ml of dichloromethane
  5. extractionthe solution was further extracted with dichloromethane (30 ml×3)
  6. washThe combined organic layer was washed with a semi-saturated saline solution
  7. dry with materialdried (anhydrous magnesium sulfate:anhydrous potassium carbonate=1:1)
  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-61ada5723d5b494ca2329699edee1267
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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