Methanol → 3,4-Didehydro naratriptan oxalate

HRID 358592ノート

反応式

HRID 358592 の反応式
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)(=[O:5])=[O:4].[OH-:17].[K+].[CH3:19][N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1.[CH3:27][OH:28]>>[C:23]([OH:26])(=[O:4])[C:27]([OH:28])=[O:17].[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[C:23]1[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH:22]=1)(=[O:5])=[O:4]

参加物

5

反応物 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 134757652-(1H-Indol-5-yl)-N-methylethane-1-sulfonamide

生成物 1

HCID 200667333,4-Didehydro naratriptan oxalate

実験手順

A solution of N-methyl-1H-indole-5-ethanesulphonamide (1.0 g) in methanol (50 ml) containing potassium hydroxide (5.6 g) and N-methyl-4-piperidone (1.0 ml) was heated at reflux for 24h, cooled, and the resulting solid filtered off (1.0 g). A sample of the solid (0.2 g) was dissolved in a hot methanolic solution of oxalic acid (0.06 g), the solution cooled, and the salt precipitated by adding ethyl acetate (20 ml) and dry ether (50 ml). The salt was filtered off, and dried in vacuo to give the title compound as a solid (0.12 g) m.p. 87°-90° (shrinks) Analysis Found: C,52.2; H,5.6; N,9.5. C17H23N3O2S.C2H2O4.0.6H2O requires C,52.5; H,6.0; N,9.7%.

後処理

  1. temperaturewas heated
  2. temperaturecooled
  3. filtrationthe resulting solid filtered off (1.0 g)
  4. dissolutionA sample of the solid (0.2 g) was dissolved in a hot methanolic solution of oxalic acid (0.06 g)
  5. temperaturethe solution cooled
  6. customthe salt precipitated
  7. additionby adding ethyl acetate (20 ml) and dry ether (50 ml)
  8. filtrationThe salt was filtered off
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-36c743241eb8401dbd961db09df5d8c6
出典データセット
uspto-grants-1991_03
特許番号
US04997841

反応ノート

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