Ethyl Acetate → N-methyl-N-phenethyl-2-(4-benzyloxy-3-formylindol-1-yl)acetamide

HRID 129691

反応式

HRID 129691 の反応式
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13]([CH:20]=[O:21])=[CH:14][NH:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:22][N:23]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24](=[O:27])[CH2:25]Br.C(OCC)(=O)C>O1CCCC1.[Cl-].[Na+].O>[CH3:22][N:23]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24](=[O:27])[CH2:25][N:15]1[C:16]2[C:12](=[C:11]([O:10][CH2:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:19]=[CH:18][CH:17]=2)[C:13]([CH:20]=[O:21])=[CH:14]1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 70158464-(benzyloxy)-1H-indole-3-carbaldehydeHCID 10753531N-methyl-N-phenethyl-2-bromoacetamide

生成物 1

HCID 10741107N-methyl-N-phenethyl-2-(4-benzyloxy-3-formylindol-1-yl)acetamide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

To a suspension of sodium hydride (1.31 g, 80% suspension in mineral oil, 43.8 mM) in 65 ml of tetrahydrofuran (THF), cooled in an ice bath, is added dropwise a solution of 4-benzyloxyindole-3-carboxaldehyde (10.2 g, 39.8 mM) in 55 ml of THF. The mixture is stirred in the cooling bath for an additional 30 minutes; N-methyl-N-phenethyl-2-bromoacetamide (15.3 g, 59.7 mM) is then added. The resulting mixture is stirred at room temperature for 18 hours. Ethyl acetate and 50% brine is added and the layers are separated. The organic layer is washed with brine, dried over magnesium sulfate and concentrated in vacuo to give crude product as a beige oil. Purification on preparative HPLC (silica gel column, 20% ethyl acetate in methylene chloride) gives N-methyl-N-phenethyl-2-(4-benzyloxy-3-formylindol-1-yl)acetamide. (m.p. 120°-122° C.)

後処理

  1. temperaturecooled in an ice bath
  2. stirringThe resulting mixture is stirred at room temperature for 18 hours
  3. customthe layers are separated
  4. washThe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give crude product as a beige oil
  8. customPurification on preparative HPLC (silica gel column, 20% ethyl acetate in methylene chloride)

出典と根拠

ORDレコード
ord-3406eb353d184e8a859d8f4cfef8029d
出典データセット
uspto-grants-1995_11
特許番号
US05468898

関連ノート

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