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

HRID 480108ノート

反応式

HRID 480108 の反応式
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C:17]([C:22]([OH:24])=[O:23])([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28].CO.[C:31]([O-])(O)=O.[Na+]>OS(O)(=O)=O.CCOC(C)=O>[CH3:31][O:23][C:22]([C:17]12[CH2:20][CH2:21][C:14]([C:7]3[NH:6][C:5]4[C:4](=[O:25])[N:3]([CH2:26][CH2:27][CH3:28])[C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=4[N:8]=3)([CH2:19][CH2:18]1)[CH2:15][CH2:16]2)=[O:24]

参加物

6

反応物 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 98865894-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid

生成物 1

HCID 98440604-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester収率 97%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 8857Ethyl Acetate溶媒

実験手順

4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid (Example 13) (1.50 g, 3.86 mmol) was combined with 60 ml of MeOH, and 10 drops of conc'd H2SO4. The reaction solution was brought to reflux until consumption of starting material ceased. Sat'd NaHCO3 was then added until neutral pH and the reaction mixture was conc'd in vacuo. The residue was taken up in EtOAc and washed with sat'd NaHCO3, brine, and dried over Na2SO4. The EtOAc solution was conc'd in vacuo to give 1.51 g (97% yield) of a white solid. (MH+=403.13)

後処理

  1. temperatureto reflux until consumption of starting material
  2. washwashed with sat'd NaHCO3, brine
  3. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-86dbde1489974cb09f8bfc93938ff989
出典データセット
uspto-grants-2003_11
特許番号
US06649600B1

反応ノート

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