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Trifluoroacetic acid → Benzyl 6-(2-hydroxy-2-propyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate

HRID 1995711
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1995711
[CH2:1]([CH:4]1[N:7]([C:8]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:6](=[O:38])[CH:5]1[C:39]([OH:42])([CH3:41])[CH3:40])[CH:2]=C.FC(F)(F)C(O)=O.O=[O+][O-]>C(OCC)(=O)C>[OH:42][C:39]([CH:5]1[C:6](=[O:38])[N:7]2[CH:4]1[CH2:1][CH:2]=[C:8]2[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])([CH3:41])[CH3:40]
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Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 24823OzoneHCID 12800412HCID 12800412, Verbindung

Produkt 1

HCID 12796946Benzyl 6-(2-hydroxy-2-propyl)-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

The cis-isomer of 4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(2-hydroxy-2-propyl)azetidin-2-one (10) (0.188 g) was dissolved in ethyl acetate (14 ml). An excess of trifluoroacetic acid (0.37 g) was added and the mixture cooled to -78° C. Ozone was passed into the reaction mixture until it was pale blue in colour. Argon was then bubbled through the solution until all the excess ozone had been removed. A solution of triphenylphosphine (0.085 g) in ethyl acetate was added and argon bubbled through the mixture for a further ten minutes. The reaction flask was then transferred to an ice bath and a saturated aqueous solution of sodium bicarbonate (20 ml) was added and the mixture stirred vigourously under argon for thirty minutes. The ethyl acetate layer was separated, washed with brine and dried.

Aufarbeitung

  1. customArgon was then bubbled through the solution until all the excess ozone
  2. customhad been removed
  3. additionA solution of triphenylphosphine (0.085 g) in ethyl acetate was added
  4. customargon bubbled through the mixture for a further ten minutes
  5. customThe reaction flask was then transferred to an ice bath
  6. additiona saturated aqueous solution of sodium bicarbonate (20 ml) was added
  7. customThe ethyl acetate layer was separated
  8. washwashed with brine
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6c0dcb9d9dc94ecbb62345b8ccf9ef33
Quelldatensatz
uspto-grants-1983_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04405637

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