2,2-Dimethoxypropane → (6S,7S)-8-oxo-2,2-dimethyl-5-methylidene-7-(1-(R)-benzyloxycarbonyloxyethyl)-3-oxa-1-azabicyclo[4.2.0]octane

HRID 1196204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196204
[OH:1][CH2:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH3:11])=[CH2:4].CO[C:25](OC)([CH3:27])[CH3:26].B(F)(F)F.CCOCC>ClCCl>[O:9]=[C:7]1[N:8]2[C@H:5]([C:3](=[CH2:4])[CH2:2][O:1][C:25]2([CH3:27])[CH3:26])[C@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH3:11]

Komponenten

5

Edukt 3

HCID 64952,2-DimethoxypropaneHCID 8000Boron trifluoride etherateHCID 15000240(3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

Produkt 1

HCID 22843873(6S,7S)-8-oxo-2,2-dimethyl-5-methylidene-7-(1-(R)-benzyloxycarbonyloxyethyl)-3-oxa-1-azabicyclo[4.2.0]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone (3.7 g) and 2,2-dimethoxypropane (1.45 g) in dry dichloromethane (26 ml) was treated with boron trifluoride-etherate (0.14 ml) at room temperature for 1.5 hours. The reaction mixture was washed successively with saturated sodium bicarbonate (15 and water (20 ml×2), and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave an oily residue, which was purified by silica gel chromatography to yield (6S,7S)-8-oxo-2,2-dimethyl-5-methylidene-7-(1-(R)-benzyloxycarbonyloxyethyl)-3-oxa-1-azabicyclo[4.2.0]octane.

Aufarbeitung

  1. washThe reaction mixture was washed successively with saturated sodium bicarbonate (15 and water (20 ml×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration of the filtrate in vacuo
  4. customgave an oily residue, which
  5. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-77f765386da447f8b8048fd551aa2463
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112966

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