phenylalaninol, (S)- → (S)-N-[1-benzyl-2-hydroxyethyl]-4-hydroxy-1-methyl-1H-indole-2-carboxamide

HRID 1829800

Reaktionsgleichung

Reaktionsgleichung von HRID 1829800
[NH2:1][C@@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][OH:4].[CH2:12]([O:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[C:23]([C:30](Cl)=[O:31])[N:24]2[CH3:29])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:5]([C@H:2]([NH:1][C:30]([C:23]1[N:24]([CH3:29])[C:25]2[C:21]([CH:22]=1)=[C:20]([O:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:28]=[CH:27][CH:26]=2)=[O:31])[CH2:3][OH:4])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:5]([C@H:2]([NH:1][C:30]([C:23]1[N:24]([CH3:29])[C:25]2[C:21]([CH:22]=1)=[C:20]([OH:19])[CH:28]=[CH:27][CH:26]=2)=[O:31])[CH2:3][OH:4])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 447213phenylalaninol, (S)-HCID 220548724-Benzyloxy-1-methyl-1H-indole-2-carbonyl chloride

Produkt 2

HCID 69272852(S)-N-[1-benzyl-2-hydroxyethyl]-4-hydroxy-1-methyl-1H-indole-2-carboxamideHCID 69276702(S)-N-[1-benzyl-2-hydroxyethyl]-4-(benzyloxy)-1-methyl-1H-indole-2-carboxamide

Versuchsvorschrift

From (S)-2-amino-3-phenylpropan-1-ol and 4-benzyloxy-1-methyl-1H-indole-2-carbonyl chloride the intermediate compound (S)-N-[1-benzyl-2-hydroxyethyl]-4-(benzyloxy)-1-methyl-1H-indole-2-carboxamide was prepared by a method analogous to that described in Example 23. MS ES (M++H)=415. Hydrogenation of this intermediate by a method analogous to that described in Example 9 gave the title compound. MS ES (M++H)=325.

Quellen und Nachweise

ORD-Eintrag
ord-6bb9a43d536b46ce973f4a40981662f4
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064143B1

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