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Water → allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1029684
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1029684
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH:9]([C:12](=O)[CH2:13][C@H:14]2[NH:17][C:16](=[O:18])[C@@H:15]2[C@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH3:20])[CH2:8]1)=[O:6])[CH:2]=[CH2:3].C(N([CH2:35][CH3:36])CC)C.O.[C:38]([O:41][CH2:42]C)(=[O:40])[CH3:39]>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH:9]([C:12]2[CH2:13][C@H:14]3[N:17]([C:16](=[O:18])[C@@H:15]3[C@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH3:20])[C:39]=2[C:38]([O:41][CH2:42][CH:35]=[CH2:36])=[O:40])[CH2:8]1)=[O:6])[CH:2]=[CH2:3]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 15117203(3S,4R)-4-[2-(1-allyloxycarbonylpyrrolidin-3-yl)-2-oxoethyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine

Produkt 1

HCID 15117359allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a solution of (3S,4R)-4-[2-(1-allyloxycarbonylpyrrolidin-3-yl)-2-oxoethyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (2.13 g) and triethylamine (1.4 ml) in dichloromethane (30 ml) was added allyl oxalyl chloride (1.1 g) at -20° C. under nitrogen, and the resulting mixture was stirred for 30 minutes at -20° C. The reaction mixture was taken up into a mixture of water and ethyl acetate. The organic layer was separated, washed in turn with water, aqueous sodium hydrogen carbonate and brine, dried over magnesium sulfate, and evaporated. To a solution of the residue in xylene (30 ml) was added triethyl phosphite (5.2 ml). The resulting mixture was heated at 90° C. for 15 hours under nitrogen, and then to the mixture was added hydroquinone (0.9 g) and the mixture was heated at 130° C. for 2 hours under nitrogen. Evaporation of the solvent gave a residue, which was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (4:1, V/V) to give allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2.9 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed in turn with water, aqueous sodium hydrogen carbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. additionTo a solution of the residue in xylene (30 ml) was added triethyl phosphite (5.2 ml)
  6. temperatureThe resulting mixture was heated at 90° C. for 15 hours under nitrogen
  7. additionto the mixture was added hydroquinone (0.9 g)
  8. temperaturethe mixture was heated at 130° C. for 2 hours under nitrogen
  9. customEvaporation of the solvent
  10. customgave a residue, which
  11. customwas chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (4:1, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-dad451f114af4cd883d41328079d46e6
Quelldatensatz
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05102877

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