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

HRID 1603443ノート

反応式

HRID 1603443 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-61ada5723d5b494ca2329699edee1267
出典データセット
uspto-grants-1999_11
特許番号
US05990101

反応ノート

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