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Dimethylacetoacetamide → tert-Butyl 2-(3-Methoxycarbonyladamant-1-ylcarbonylamino)-6-(N,N-dimethylaminocarbonyl)hex-4-ynoate

HRID 1242839
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1242839
[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([NH:17][CH:18]([CH2:26][C:27]#[CH:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4].[CH3:29][N:30]([CH3:37])[C:31](=[O:36])[CH2:32]C(C)=O>C1C=CC=CC=1.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([NH:17][CH:18]([CH2:26][C:27]#[C:28][CH2:32][C:31]([N:30]([CH3:37])[CH3:29])=[O:36])[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 16278DimethylacetoacetamideHCID 21940505tert-Butyl 2-(3-methoxycarbonyladamant-1-ylcarbonylamino)pent-4-ynoate

Produkt 1

HCID 21940554tert-Butyl 2-(3-Methoxycarbonyladamant-1-ylcarbonylamino)-6-(N,N-dimethylaminocarbonyl)hex-4-ynoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 241
Benzene
Lösungsmittel

Versuchsvorschrift

tert-Butyl 2-(3-methoxycarbonyladamant-1-ylcarbonylamino)pent-4-ynoate (0.44 g) was dissolved in 0.8 mL of dry benzene under nitrogen. To this solution was added a catalytic amount of CuSO4 and the reaction mixture was brought to reflux. N,N-Dimethyl acetoacetamide was added dropwise in excess. Evolution of nitrogen was observed. The addition was complete after 30 min. The reaction was then heated for another 30 min. After cooling the reaction mixture, the solvent was evaporated under reduced pressure and the crude product was purified on a prep plate (silica gel; EtOAc/hexanes, 2:3) to afford the title compound as an oil.

Aufarbeitung

  1. temperatureto reflux
  2. additionThe addition
  3. temperatureThe reaction was then heated for another 30 min
  4. temperatureAfter cooling the reaction mixture
  5. customthe solvent was evaporated under reduced pressure
  6. customthe crude product was purified on a prep plate (silica gel; EtOAc/hexanes, 2:3)

Quellen und Nachweise

ORD-Eintrag
ord-9ee51b8828e64373a76bf75068b9ca6f
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07115768B2

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