Triethylamine → 3-{beta-(1-Methylimidazole-4-yl)acryloyl}amino-delta-valerolactam

HRID 465348ノート

反応式

HRID 465348 の反応式
C(N(CC)CC)C.O.[OH:9]N1C2C=CC=CC=2N=N1.[CH:19]1([N:25]=[C:26]=[N:27][CH:28]2[CH2:33]C[CH2:31][CH2:30][CH2:29]2)CCCCC1.[NH2:34][CH:35]1[CH2:41][CH2:40][NH:39][C:37](=[O:38])[CH2:36]1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:19][N:25]1[CH:33]=[C:28]([CH:29]=[CH:30][C:31]([NH:34][CH:35]2[CH2:41][CH2:40][NH:39][C:37](=[O:38])[CH2:36]2)=[O:9])[N:27]=[CH:26]1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 199802604-Aminopiperidin-2-one

生成物 1

HCID 538765823-{beta-(1-Methylimidazole-4-yl)acryloyl}amino-delta-valerolactam収率 73%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of β-(1-methylimidazole-4-yl)acrylrate hydrochloride (7 g, 37.1 mmole) in dimethylformamide (60 ml) was added triethylamine (7.51 g, 74.2 mmole) and 1-hydroxybenzotriazole hydrate (6.25 g, 40.8 mmole) and the mixture was ice-cooled, and then a solution of dicyclohexylcarbodiimide (8.42 g, 40.8 mmole) in dimethylformamide (15 ml) was added dropwise. After stirring at 80° C. for 30 minutes, followed by at room temperature for 30 minutes, 3-amino-δ-valerolactam (5.08 g, 44.5 mmole) was added to the reaction mixture which was heated with stirring for 13 hours. After cooling to room temperature, a sodium bicarbonate solution was added to the mixture which was extracted with a chloroform-methanol mixed solvent. After drying over magnesium sulfate, the solvent was removed under reduced pressure. The residue was subjected to silica gel flash chromatography and then recrystallized from ethanol/chloroform to obtain the titled compound (6.72 g, 73.0%).

後処理

  1. temperaturecooled
  2. waitfollowed by at room temperature for 30 minutes
  3. temperaturewas heated
  4. stirringwith stirring for 13 hours
  5. temperatureAfter cooling to room temperature
  6. extractionwas extracted with a chloroform-methanol mixed solvent
  7. dry with materialAfter drying over magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customrecrystallized from ethanol/chloroform

出典と根拠

ORDレコード
ord-cb67409c2f3945e1b3a66c44315c4520
出典データセット
uspto-grants-1992_10
特許番号
US05153201

反応ノート

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