Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:16][C:17]([OH:19])=O)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C(C1NC=CN=1)(C1NC=CN=1)=O.[C:33]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])(=[O:38])[CH2:34]C([O-])=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]([NH:5][C:6]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:7])[CH2:16][C:17](=[O:19])[CH2:34][C:33]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of N-CBZ L-aspartic acid 1-methyl ester (1.00 g, 3.55 mmol) in dry tetrahydrofuran (17 mL) is added carbonyl diimidazole (634.1 mg, 3.91 mmol). The mixture is stirred at room temperature for 6 hr then the magnesium salt of mono-tert butyl malonate (1.339 g, 3.91 mmol) (prepared according to Angew. Chem. Int. Ed. Engl. 1979, 18(1), 72-74) is added. The mixture is stirred at room temperature for another 20 h, then concentrated in vacuum. The residue is partitioned between ether (60 mL) and 0.5 N HCl (60 mL). The organic layer is washed with saturated NaHCO3 solution (50 mL) then dried over magnesium sulfate and concentrated in vacuum. The residue is purified over 35 g of silica gel, eluted with EtOAc:Heptane (1:1) to afford (S)-2-Benzyloxycarbonylamino-4-oxo-hexanedioic acid 6-tert-butyl ester 1-methyl ester (1.17 g, 87%).
Aufarbeitung
- stirringThe mixture is stirred at room temperature for another 20 h
- concentrationconcentrated in vacuum
- customThe residue is partitioned between ether (60 mL) and 0.5 N HCl (60 mL)
- washThe organic layer is washed with saturated NaHCO3 solution (50 mL)
- dry with materialthen dried over magnesium sulfate
- concentrationconcentrated in vacuum
- customThe residue is purified over 35 g of silica gel
- washeluted with EtOAc:Heptane (1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-c41057ce537c4b0eadf8e34d68308ee8
- Quelldatensatz
- uspto-grants-2009_01
- Patentnummer
- US07482448B2
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