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Diethyl Ether → 4-Nitrobenzyl (5r)-6-[(acetyloxy)(5-methyl-7,8-dihydro-6h-cyclopenta[e] [1,2,4]triazolo [1,5-a]pyrimidin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1744960
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1744960
[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH:11]=[O:12])[N:10]=[C:6]2[N:5]=[C:4]2[CH2:13][CH2:14][CH2:15][C:3]=12.[N+:16]([C:19]1[CH:37]=[CH:36][C:22]([CH2:23][O:24][C:25]([C:27]2[N:28]3[C@H:31]([S:32][CH:33]=2)[C@@H:30]([Br:34])[C:29]3=[O:35])=[O:26])=[CH:21][CH:20]=1)([O-:18])=[O:17].[Mg+2].[Br-].[Br-].[O:41](CC)[CH2:42][CH3:43].C(OC(=O)C)(=O)C>C(OCC)(=O)C.CCN(CC)CC.C(#N)C.C1COCC1>[C:42]([O:12][CH:11]([C:9]1[N:10]=[C:6]2[N:7]=[C:2]([CH3:1])[C:3]3[CH2:15][CH2:14][CH2:13][C:4]=3[N:5]2[N:8]=1)[C:30]1([Br:34])[C:29](=[O:35])[N:28]2[C@@H:31]1[S:32][CH:33]=[C:27]2[C:25]([O:24][CH2:23][C:22]1[CH:36]=[CH:37][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=1)=[O:26])(=[O:41])[CH3:43]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 5

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 82241Magnesium BromideHCID 11280588(5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl esterHCID 222245208-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[-1,5-a]pyrimidine-2-carbaldehyde

Produkt 1

HCID 69608429
4-Nitrobenzyl (5r)-6-[(acetyloxy)(5-methyl-7,8-dihydro-6h-cyclopenta[e] [1,2,4]triazolo [1,5-a]pyrimidin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

8-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde (153 mg, 0.75 mmol) and the dry THF solution (20 mL) of (5R, 6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (385 mg, 1 mmol) were added successively to the dry acetonitrile (15 mL) solution of anhydrous MgBr2: O(Et)2 (1.2 g, 3.0 mmol)under an argon atmosphere at room temperature. After cooling to −20° C., Et3N (2.0 mL) was added in one portion. The reaction vessel was covered with foil to exclude light. The reaction mixture was stirred for 2 h at −20° C. and treated with acetic anhydride (1.04 mL) in one portion. The reaction mixture was warmed to 0° C. and stirred for 15 h at 0° C. The mixture was diluted with ethyl acetate and washed with 5% citric acid aqueous solution, saturated sodium hydrogen carbonate, and brine. The organic layer was dried (MgSO4) and filtered through a pad of Celite. The pad was washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with ethyl acetate:hexane (1:1). Collected fractions were concentrated under reduced pressure and the mixture of diastereomers were taken to the next step. Pale yellow amorphous solid; Yield: 200 mg, 42%; (M+H) 631.

Aufarbeitung

  1. customat room temperature
  2. temperatureThe reaction mixture was warmed to 0° C.
  3. stirringstirred for 15 h at 0° C
  4. washwashed with 5% citric acid aqueous solution, saturated sodium hydrogen carbonate, and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered through a pad of Celite
  7. washThe pad was washed with ethyl acetate
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. washthe column was eluted with ethyl acetate:hexane (1:1)
  10. concentrationCollected fractions were concentrated under reduced pressure
  11. additionthe mixture of diastereomers

Quellen und Nachweise

ORD-Eintrag
ord-682e8a9c7f34401bbd8284104a21eefc
Quelldatensatz
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07018997B2

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