Tetrahydrofuran → N-Propionylserotonin

HRID 324629

反応式

HRID 324629 の反応式
[CH:1]1[C:6]([OH:7])=[CH:5][C:4]2[C:8]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:10][C:3]=2[CH:2]=1.Cl.[O:15]1C[CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+].C(OC(=O)CC)(=O)CC>O>[OH:7][C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:1]=1)[NH:10][CH:9]=[C:8]2[CH2:11][CH2:12][NH:13][C:16](=[O:15])[CH2:17][CH3:18]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 31263Propionic anhydrideHCID 160436Serotonin Hydrochloride

生成物 1

HCID 594440N-Propionylserotonin収率 98%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of serotonin hydrochloride (10 g, 47.5 mmol.) in water (50 mL) were added, under argon atmosphere, tetrahydrofuran (20 mL) and a solution of sodium carbonate (5.3 g) in water (20 mL). The mixture was cooled to 0° C., to which was added propionic anhydride (6.2 g, 49.9 mmol.). The mixture was stirred for 2 hours at room temperature. The reaction mixture was subjected to extraction with ethyl acetate. The extract solution was washed with 1N HCl, a saturated aqueous solution of sodium hydrogencarbonate and water, which was dried and then concentrated to afford the title compound (yield 10.0 g, 98.0%) as an oily product. This compound was used, without refining further, for the subsequent reaction.

後処理

  1. extractionThe reaction mixture was subjected to extraction with ethyl acetate
  2. washThe extract solution was washed with 1N HCl
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, which was dried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-cebb2af3cf244302b2006f585506baab
出典データセット
uspto-grants-2001_04
特許番号
US06218429B1

関連ノート

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