Sodium Hydroxide → 3-Amino-6-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

HRID 2242905ノート

反応式

HRID 2242905 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[C:16]3[C:21](=[N:22][CH:23]=2)[N:20]=CN(C)[C:17]3=[O:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:26].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:23]=[N:22][C:21]([NH2:20])=[C:16]([C:17]([OH:25])=[O:26])[N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 66745135Tert-butyl 4-(3-methyl-4-oxo-3,4-dihydropteridin-6-yl)piperazine-1-carboxylate

生成物 1

HCID 667448533-Amino-6-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrazine-2-carboxylic acid収率 67%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred suspension of 4-(3-methyl-4-oxo-3,4-dihydro-pteridin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester (428 mg, 1.24 mmol; see Example 16 (d) above) in methanol (5 mL) was added 10% aqueous sodium hydroxide (5 mL). The reaction mixture was stirred overnight at room temperature and concentrated in vacuo. The residue was then diluted with water and neutralized with formic acid (pH 7). The resulting precipitate was removed by filtration and the filtrate was acidified with formic acid (pH 4) and extracted with methylene chloride. The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford 5′-amino-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4,6′-dicarboxylic acid 4tert-butyl ester as a yellow solid (265 mg, 67%). 1H NMR (300 MHz, CDCl3) δ1.49 (s, 9 H), 3.38 (t, J=5.4 Hz, 4H), 3.60 (t, J=5.4 Hz, 4H), 6.06 (br s, 1H), 8.15 (s, 1 H); 13C NMR (75 MHz, CDCl3) δ28.39, 46.16, 80.29, 116.40, 138.73, 147.39, 149.67, 154.59, 165.95.

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue was then diluted with water and neutralized with formic acid (pH 7)
  3. customThe resulting precipitate was removed by filtration
  4. extractionextracted with methylene chloride
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5a9a0e13943642de967134d67224cca3
出典データセット
uspto-grants-2010_03
特許番号
US07674791B2

反応ノート

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