Sulfuric Acid → Ethyl 3-(methoxycarbonylacetamido)-3-phenylbutyrate

HRID 1196418

Reaktionsgleichung

Reaktionsgleichung von HRID 1196418
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].O[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].S(=O)(=O)(O)[OH:24]>>[CH3:7][O:6][C:4]([CH2:3][C:1]([NH:2][C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:24])=[O:5]

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 7747Methyl cyanoacetateHCID 220801Ethyl 3-hydroxy-3-phenylbutanoate

Produkt 1

HCID 53957516Ethyl 3-(methoxycarbonylacetamido)-3-phenylbutyrate

Versuchsvorschrift

Concentrated sulphuric acid (80 ml) was added at 0°-5° C. to a stirred solution of methyl cyanoacetate (28 ml) and ethyl 3-hydroxy-3-phenylbutyrate (65 g) and the mixture stirred at ambient temperature for 18 hours. The mixture was added to crushed ice (250 g) and the acidic mixture extracted with dichloromethane (3×100 ml). The combined extracts were washed with water (4×250 ml), dried over sodium sulphate and evaporated under reduced pressure to give ethyl 3-(methoxycarbonylacetamido)-3-phenylbutyrate (43.16 g), as a clear brown oil.

Aufarbeitung

  1. additionThe mixture was added
  2. extractionthe acidic mixture extracted with dichloromethane (3×100 ml)
  3. washThe combined extracts were washed with water (4×250 ml)
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b3b76e764dbf473c8344cc2d8f838ec0
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05114461

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