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

HRID 1603443노트

반응식

HRID 1603443 반응식
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]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19605053Allyl sulfamoylcarbamateHCID 19605134{3-Methylimidazo[4,3-b][1,3]thiazol-2-yl}methanol

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-61ada5723d5b494ca2329699edee1267
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05990101

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