(R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acid → (R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid
Reaktionsgleichung
[CH2:1]([N:8]([C@H:13]([CH2:17][OH:18])[C:14]([OH:16])=[O:15])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(C)(C)C.[K+]>C(O)(C)(C)C>[CH2:1]([N:8]1[C:9](=[O:12])[CH2:10][O:18][CH2:17][C@@H:13]1[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
To a solution of (R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acid (1.53 g, 5.63 mmol) in tert-butanol was added potassium tert-butanolate and the reaction mixture heated to 110° C. for three h, then cooled to room temperature and concentrated to dryness. The residue was acidified with 1 N HCl to pH 1 and the aqueous solution extracted with EtOAc (3×250 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 10 to 30% CH3OH in CH2Cl2 with 1% acetic acid) to provide (R)-4-benzyl-5-oxomorpholine-3-carboxylic acid (780 mg, 59%) as a yellow foam. 1H NMR and MS consistent.
Aufarbeitung
- temperaturecooled to room temperature
- concentrationconcentrated to dryness
- extractionthe aqueous solution extracted with EtOAc (3×250 mL)
- dry with materialThe organic layer was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography (silica gel, 10 to 30% CH3OH in CH2Cl2 with 1% acetic acid)
Quellen und Nachweise
- ORD-Eintrag
- ord-492b44967f864f49bed5e17b652b7f80
- Quelldatensatz
- uspto-grants-2011_01
- Patentnummer
- US07863271B2
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