Water → 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid

HRID 480160ノート

反応式

HRID 480160 の反応式
C[O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13](=O)[NH:14][C:15]3[C:16](=[O:29])[N:17]([CH2:26][CH2:27][CH3:28])[C:18](=[O:25])[N:19]([CH2:22][CH2:23][CH3:24])[C:20]=3[NH2:21])([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:4].C(O)(C)C.[OH-].[K+].O>C1(C)C=CC=CC=1>[O:25]=[C:18]1[N:19]([CH2:22][CH2:23][CH3:24])[C:20]2[N:21]=[C:13]([C:8]34[CH2:11][CH2:12][C:5]([C:3]([OH:2])=[O:4])([CH2:10][CH2:9]3)[CH2:6][CH2:7]4)[NH:14][C:15]=2[C:16](=[O:29])[N:17]1[CH2:26][CH2:27][CH3:28]

参加物

6

反応物 4

HCID 962WaterHCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 865917464-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydropyrimidin-5-ylcarbamoyl)bicyclo[2.2.2]octane-1-carboxylic acid methyl ester

生成物 1

HCID 98865894-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
17.5 °C

実験手順

4-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (VII, Example 83b, 0.760 kg) and isopropanol (3.62 l) are combined. The mixture is stirred under nitrogen and potassium hydroxide (2 M, 3.62 l) is added. The contents are heated at reflux for 3 hr (test for reaction completion by NMR). The mixture is then allowed to cool to 10 to 25° C. Water (8.48 l) is added followed by toluene (0.95 l) and the contents are stirred vigorously for 5 to 15 minutes. The layers are separated. Extraction with toluene (0.95 l) is performed two additional times. The aqueous phase is then cooled to between 0 and 10° C. and acidified with concentrated hydrochloric acid (0.562 l). The mixture is stirred at between 0 and 10° C. for 60 minutes. Solid product is collected by filtration and dried under reduced pressure at 50 to 60° C. to give the title compound.

後処理

  1. temperatureThe contents are heated
  2. temperatureat reflux for 3 hr
  3. custom(test for reaction completion by NMR)
  4. stirringthe contents are stirred vigorously for 5 to 15 minutes
  5. customThe layers are separated
  6. extractionExtraction with toluene (0.95 l)
  7. temperatureThe aqueous phase is then cooled to between 0 and 10° C.
  8. stirringThe mixture is stirred at between 0 and 10° C. for 60 minutes
  9. filtrationSolid product is collected by filtration
  10. customdried under reduced pressure at 50 to 60° C.

出典と根拠

ORDレコード
ord-c1686055dde8454bafa301d7b11be5b2
出典データセット
uspto-grants-2003_11
特許番号
US06649600B1

反応ノート

読み込み中…