Tetrahydrofuran → Methyl bis-(1-naphthylmethyl)acetyl-(alpha-methyl-D-tryptophan)
Reaktionsgleichung
[CH3:1][NH:2][C@@:3]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[C:18]1([CH2:28][CH:29]([CH2:33][C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][CH:35]=2)[C:30](Cl)=O)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.CCN(CC)CC.C1C[O:54]CC1>>[CH3:30][C:29]([CH2:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1)([CH2:28][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C:1]([NH:2][C@@:3]([CH3:17])([C:14]([OH:16])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:54]Komponenten
5
Versuchsvorschrift
A solution of 2.0 g (8.6 mmol) of methyl α-methyl-D-tryptophan in 30 mL THF was treated with 3.09 g (8.6 mmol) of bis-(1-naphthylmethyl)acetyl chloride (J. Med. Chem., 35:1032 (1992)) followed by 1.2 mL (8.6 mmol) of Et3N. After stirring at room temperature for 2 days, the solvent was removed under reduced pressure and the residue taken up in EtOAc and washed with 1HCl, H2O, saturated NaHCO3, and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure gave 4.77 g of the crude product. Recrystallization from CH3CN/H2O gave 4.24 g (88.9% yield) of the product as a cream solid, mp 193°-195° C. The structure was confirmed by NMR and mass spectroscopy.
Aufarbeitung
- customthe solvent was removed under reduced pressure
- washwashed with 1HCl, H2O, saturated NaHCO3, and saturated NaCl
- dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
- customgave 4.77 g of the crude product
- customRecrystallization from CH3CN/H2O
Quellen und Nachweise
- ORD-Eintrag
- ord-7ed07fbcda7a47d681ad90327e7f0d90
- Quelldatensatz
- uspto-grants-1997_03
- Patentnummer
- US05610177
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