2,3-Dihydroxybutanedioic Acid → (-)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]imidazole (-)-tartrate

HRID 1658274

反応式

HRID 1658274 の反応式
[C:1]1([CH:7]2[N:11]3[CH2:12][CH2:13][NH:14][C:10]3=[N:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[C:17]([OH:26])(=[O:25])[CH:18]([CH:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19]>CC(C)=O>[C:22]([CH:20]([CH:18]([C:17]([OH:26])=[O:25])[OH:19])[OH:21])([OH:24])=[O:23].[C:1]1([CH:7]2[N:11]3[CH2:12][CH2:13][NH:14][C:10]3=[N:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 887Methanol2 回HCID 163316Deximafen

生成物 1

HCID 21529050(-)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]imidazole (-)-tartrate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a stirred solution of 10.7 parts of (±)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]imidazole in 20 parts of methanol is added a warm solution of 8.6 parts of (+)-tartaric acid in 20 parts of methanol. The whole is diluted with 80 parts of acetone and the product is allowed to crystallize. The precipitated fraction is filtered off [about 5.6 parts of crude (+)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]-imidazole (+)-tartrate - α(1% MeOH): +87.3°]and set aside. The filtrate is evaporated in vacuo. The residue is dissolved in water and the free base is liberated. It is extracted with chloroform and the latter is dried and evaporated. The residue is dissolved in 28 parts of methanol and to this solution is added a warm solution of 5.7 parts of (-)-tartaric acid in 60 parts of methanol. The product is allowed to crystallize. It is filtered off and recrystallized from a mixture of 8 parts of methanol and 16 parts of acetone till a constant rotation, yielding about 4.3 parts of (-)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]imidazole(-)-tartrate; α(1% MeOH): -89.97°. A sample of 4.2 parts of (-)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]imidazole(-)-tartrate is dissolved in water and the free base is liberated. After extraction with chloroform, the latter is dried and evaporated. The residue is crystallized from acetone, yielding about 0.7 parts of (-)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]-imidazole; m.p. 153.2°C.; α(1% MeOH): -211.49°. The free base together with the residue of the evaporated mother-liquor is converted into the hydrochloride salt yielding about 1.9 parts of (-)-2,3,5,6-tetrahydro-5phenyl-1H-imidazo[1,2-a]-imidazole hydrochloride; m.p. 277.1°C.; α(1% MeOH): -115.79°.

後処理

  1. customto crystallize
  2. filtrationThe precipitated fraction is filtered off [about 5.6 parts of crude (+)-2,3,5,6-tetrahydro-5-phenyl-1H-imidazo[1,2-a]-imidazole (+)-tartrate - α(1% MeOH)
  3. custom+87.3°
  4. customThe filtrate is evaporated in vacuo
  5. dissolutionThe residue is dissolved in water
  6. extractionIt is extracted with chloroform
  7. customthe latter is dried
  8. customevaporated
  9. dissolutionThe residue is dissolved in 28 parts of methanol and to this solution
  10. additionis added a warm solution of 5.7 parts of (-)-tartaric acid in 60 parts of methanol
  11. customto crystallize
  12. filtrationIt is filtered off
  13. customrecrystallized from a mixture of 8 parts of methanol and 16 parts of acetone till a constant rotation

出典と根拠

ORDレコード
ord-5e562a909fcf4d4ca0745cfcd662db07
出典データセット
uspto-grants-1976_06
特許番号
US03963718

関連ノート

読み込み中…