Acetic Anhydride → 2,3-Dihydromelatonin

HRID 612531ノート

反応式

HRID 612531 の反応式
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH:6]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH2:5]1)(=O)C.COC1C=C2C(=CC=1)NCC2CCNC(=O)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(OC(=O)C)(=O)C.[F:60][C:61]([F:86])([F:85])[S:62]([N:65]1[C:73]2[C:68](=[CH:69][C:70]([O:74][CH3:75])=[CH:71][CH:72]=2)[CH:67]([CH2:76][CH2:77][N:78](C(C)=O)[C:79](=[O:81])[CH3:80])[CH2:66]1)(=[O:64])=[O:63]>ClCCl.C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:14][O:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][CH2:5][CH:6]2[CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19].[F:86][C:61]([F:60])([F:85])[S:62]([N:65]1[C:73]2[C:68](=[CH:69][C:70]([O:74][CH3:75])=[CH:71][CH:72]=2)[CH:67]([CH2:76][CH2:77][NH:78][C:79](=[O:81])[CH3:80])[CH2:66]1)(=[O:63])=[O:64]

参加物

10

反応物 5

HCID 7918Acetic AnhydrideHCID 67749Trifluoromethanesulfonic anhydrideHCID 101308722,3-DihydromelatoninHCID 23283701N-[2-(1-acetyl-5-methoxyindolin-3-yl)ethyl]acetamideHCID 69944386N-[2-(1-trifluoromethanesulphonyl-5-methoxyindolin-3-yl)ethyl]diacetamide

生成物 2

HCID 101308722,3-DihydromelatoninHCID 23283707N-[2-(1-trifluoromethanesulphonyl-5-methoxyindolin-3-yl)ethyl]acetamide

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

N-[2-(5-Methoxyindolin-3-yl)ethyl]acetamide is prepared by the method described for the synthesis of N-[2-(1-acetyl-5-methoxyindolin-3-yl)ethyl]acetamide. The intermediate N-[2-(1-trifluoromethanesulphonyl-5-methoxyindolin-3-yl)ethyl]acetamide is prepared by reacting N-[2-(5-methoxyindolin-3-yl)ethyl]acetamide with trifluoromethanesulphonic anhydride in dichloromethane at -78° C. in the presence of triethylamine. The final acylation is carried out with acetic anhydride in refluxing toluene for 24 h, and allows N-[2-(1-trifluoromethanesulphonyl-5-methoxyindolin-3-yl)ethyl]diacetamide to be obtained.

後処理

  1. customat -78° C.
  2. customto be obtained

出典と根拠

ORDレコード
ord-6b43f3c4dc514d088fbc6947e47a79dc
出典データセット
uspto-grants-1999_12
特許番号
US06004991

反応ノート

読み込み中…