Acetone → HCID 10989578, Verbindung

HRID 1393466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1393466
[NH2:1][C@H:2]([C:7]([O:9]C)=[O:8])CC([O-])=O.[C:11]([O-])([O-])=[O:12].[Na+].[Na+].[C:17]1([CH2:23][CH2:24][C:25](Cl)=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl.C[C:30]([CH3:32])=[O:31]>O>[CH3:11][O:12][C:30](=[O:31])[CH2:32][CH:2]([NH:1][C:25](=[O:26])[CH2:24][CH2:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:7]([OH:9])=[O:8]

Komponenten

7

Edukt 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 64801Benzenepropanoyl chlorideHCID 57352248(3S)-3-Amino-4-methoxy-4-oxobutanoate

Produkt 1

HCID 10989578HCID 10989578, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Methyl L-aspartate (15.0 g, 0.082 mol), DI water (245 mL), acetone (20 mL), and Na2CO3 (30.8 g, 0.286 mol) were combined and cooled the solution to 5° C. 3-Phenyl-propionyl chloride (13.3 mL, 0.089 mol) was added dropwise via addition funnel over 10 min. The reaction was allowed to warm to ambient temperature and stir for 2 h. The reaction became very thick during this time. Added conc. HCl (50 mL) to the slurry until the pH was ≦4.0. The reaction mixture was extracted with CH2Cl2 (3×). The organic phase was washed with water and then dried (MgSO4), filtered and concentrated under reduced pressure. The clear, colorless oil was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.92 (br s, 1H), 7.28-7.17 (m, 5H), 6.57 (d, J=7.6 Hz, 1H), 4.87 (m, 1H), 3.67 (s, 3H), 2.96 (t, J=7.6 Hz, 2H), 2.89 (A of ABX, JAB=17.6 Hz, JAX=4.8 Hz, 1H), 2.88 (B of ABX, JBA=17.6 Hz, JBX=4.0 Hz, 1H), 2.69 (t, J=7.6 Hz, 2H); MS (EI+) 280 (M+H), 302 (M+H+Na).

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. extractionThe reaction mixture was extracted with CH2Cl2 (3×)
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe clear, colorless oil was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-38be6efefd9946c2bffdd8636e17ba3c
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345070B2

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