(+-)-5-Hydroxytryptophan → HCID 136045351, Verbindung

HRID 1534968

Reaktionsgleichung

Reaktionsgleichung von HRID 1534968
[CH:1]1[C:6]([OH:7])=[CH:5][C:4]2[C:8]([CH2:11][CH:12]([NH2:16])[C:13]([OH:15])=[O:14])=[CH:9][NH:10][C:3]=2[CH:2]=1.CS(C)=O.[O:21]=[C:22]1[NH:30][CH:29]=[N:28][C:27]2[N:26]([CH2:31][CH2:32][C:33](OC3C=CC([N+]([O-])=O)=CC=3)=[O:34])[CH:25]=[N:24][C:23]1=2>CC(C)=O>[O:21]=[C:22]1[NH:30][CH:29]=[N:28][C:27]2[N:26]([CH2:31][CH2:32][C:33]([NH:16][CH:12]([CH2:11][C:8]3[C:4]4[C:3](=[CH:2][CH:1]=[C:6]([OH:7])[CH:5]=4)[NH:10][CH:9]=3)[C:13]([OH:15])=[O:14])=[O:34])[CH:25]=[N:24][C:23]1=2

Komponenten

5

Edukt 3

HCID 144(+-)-5-HydroxytryptophanHCID 679Dimethyl SulfoxideHCID 1359739573-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester

Produkt 1

HCID 136045351HCID 136045351, VerbindungAusbeute 7,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

100 mg (0.500 mmol) of DL-5-hydroxytryptophan and 3 ml of dry dimethylsulfoxide were placed in a 25 ml round bottom flask equipped with a magnetic stirring bar and stopper. Then 150 mg (0.456 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester (AIT-0081) were added and the heterogeneous mixture was stirred for 2.5 hours at room temperature in the closed flask. The mixture became completely homogeneous. The reaction mixture was poured into 20 ml of acetone and a semi-solid precipitate was obtained by filtration. The crude product was washed twice with 2 ml of acetone. The solid was resuspended in 10 ml of acetone and the insoluble material was removed by filtration. The acetone solution was evaporated to dryness. The yield of product 2-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-3-(5-hydroxyl-1H-indol-3-yl)-propionic acid (AIT-0111) was 15 mg. Yield: 7.3% (Purity 93 %).

Aufarbeitung

  1. customequipped with a magnetic stirring bar
  2. customa semi-solid precipitate was obtained by filtration
  3. washThe crude product was washed twice with 2 ml of acetone
  4. customthe insoluble material was removed by filtration
  5. customThe acetone solution was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b67a98265dd44c46b9b57530daeaf694
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05091432

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