Succinic anhydride → 4-oxo-4-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)butanoic acid

HRID 1864032

反応式

HRID 1864032 の反応式
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]3[CH:13]=[CH:14][CH:15]=[C:8]23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[C:23]1(=[O:29])[O:28][C:26](=[O:27])[CH2:25][CH2:24]1.CC(=O)OCC.CO>CC#N.CC(=O)OCC>[O:29]=[C:23]([N:12]1[CH2:11][CH2:10][N:9]2[CH:13]=[CH:14][CH:15]=[C:8]2[CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:24][CH2:25][C:26]([OH:28])=[O:27]

参加物

7

反応物 4

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 27709101-phenyl-1H,2H,3H,4H-pyrrolo(1,2-a)pyrazineHCID 21584119Ethylacetate methanol

生成物 1

HCID 427793334-oxo-4-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)butanoic acid収率 44%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-Phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine (A2) (396 mg, 2.0 mmol) and NEt3 (277 μl, 2.0 mmol) were added to a suspension of succinic anhydride (176 mg, 1.76 mmol) in MeCN (28 ml), and stirring was carried out for 16 h at RT. The mixture was then diluted with EA (30 ml) and washed with 2N hydrochloric acid (2×5 ml). The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was taken up in EA (50 ml) and again washed with 2N hydrochloric acid (20 ml) and then with a sat. aq. sodium carbonate solution (2×30 ml). The organic phase was again dried over MgSO4, filtered and concentrated in vacuo. CC (EA/MeOH 3:1) with the residue yielded 230 mg (0.77 mmol, 44%) of 4-oxo-4-(1-phenyl-3,4-dihydro-pyrrolo[1,2-a]pyrazin-2(1H)-yl)butanoic acid (S3).

後処理

  1. washwashed with 2N hydrochloric acid (2×5 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washagain washed with 2N hydrochloric acid (20 ml)
  6. dry with materialThe organic phase was again dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0321d5d80ac8403bbae5e5d5c7fa9c6f
出典データセット
uspto-grants-2009_12
特許番号
US07625900B2

関連ノート

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