Methanol → 3,4-Didehydro naratriptan oxalate

HRID 358592노트

반응식

HRID 358592 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

HCID 200667333,4-Didehydro naratriptan oxalate

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-36c743241eb8401dbd961db09df5d8c6
출처 데이터셋
uspto-grants-1991_03
특허 번호
US04997841

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