Citric Acid → HCID 53987300, Verbindung
Reaktionsgleichung
[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:2]([C:7](OC)=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6].[Cl-].[Li+].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.C(O)C>[C:14]([O:13][C:11]([NH:1][C@H:2]([CH2:3][CH2:4][CH2:5][CH3:6])[CH2:7][OH:8])=[O:12])([CH3:17])([CH3:16])[CH3:15]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of Boc-DNle-OMe (4.23 g) in dry THF (30 ml) were added lithium chloride (0.85 g), sodium borohydride (0.76 g) and dry ethanol (60 ml), and the mixture was stirred at the same temperature for 2 h and at room temperature over night. The mixture was cooled with ice-water, adjusted to pH 3 by the gradual addition of 10% aq. citric acid, and concentrated in vacuo. Water (200 ml) was added to the residue, and the mixture was extracted with dichloromethane (50 ml×3). The combined organic layers were washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel chromatography (Merck, Kieselgel 60) with hexane/ethyl acetate=1/1 for elution to give the product (2.95 mg).
Aufarbeitung
- concentrationconcentrated in vacuo
- additionWater (200 ml) was added to the residue
- extractionthe mixture was extracted with dichloromethane (50 ml×3)
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- customevaporated in vacuo
- customThe residue was purified by silica gel chromatography (Merck, Kieselgel 60) with hexane/ethyl acetate=1/1 for elution
Quellen und Nachweise
- ORD-Eintrag
- ord-5fcf2839cc364d20baf6ca2c047b74d2
- Quelldatensatz
- uspto-grants-1997_03
- Patentnummer
- US05614498
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