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Ammonium Chloride → HCID 44596871, Verbindung

HRID 553556
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 553556
[C:1]([N:9]1[C@H:13]([CH3:14])[C:12](=[O:15])[O:11][C@H:10]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=1.[NH4+].[Cl-]>C1COCC1>[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][C@:13]2([CH3:14])[C:12](=[O:15])[O:11][C@@H:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:9]2[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:36][CH:35]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 1650214-Methoxybenzyl bromideHCID 2733832Lithium hexamethyldisilazaneHCID 13818180(2S,4R)-3-Benzoyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one

Produkt 1

HCID 44596871HCID 44596871, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Compound 2.2 (6.35 g, 0.023 mol) in 50 mL of THF at −78° C. was added over 20 min to a solution of LHMDS in THF (25 mL of 1 M solution in THF). After 10 min, 1.1 eq. of 4-methoxybenzyl bromide (25 mmol, 5 mL) was added in one portion. The mixture was stirred at −78° C. for 3 h and then room temperature overnight. Saturated NH4Cl solution was added, the THF was removed in vacuo, 100 mL of Et2O was added and the phases were separated. The organic layer was washed with 50 mL of NaHCO3 solution and brine. After drying (Na2SO4), filtration and removal of the solvent, the residue was purified by chromatography using Si Gel ISCO column with 9% EtOAc in Hexanes as eluent. Concentration of the product fractions gave 7.4 g (82%) of 2.3 as a white solid. MP 128-129° C.; [α]25D=−260 (c 0.8, MeOH); 1H NMR δ 7.27 (1H, d, J=8 Hz), 7.19-7.14 (2H, m), 7.09-7.05 (4H, m), 6.94 (d, 2H, J=8 Hz), 6.76-6.72 (m, 4H), 5.68 (s, 1H), 3.88 (d, 1H, J=12 Hz), 3.86 (s, 3H), 3.27 (d, 1H, J=12 Hz), 2.14 (s, 3H); C NMR 175.1, 169.4, 159.6, 136.7, 131.5, 130.1, 130.0, 128.8, 128.7, 128.2, 127.2, 126.3, 114.6, 90.7, 65.9, 55.8, 40.5, 24.6; ESI MS 402 (M+1).

Aufarbeitung

  1. customroom temperature overnight
  2. customthe THF was removed in vacuo, 100 mL of Et2O
  3. additionwas added
  4. customthe phases were separated
  5. washThe organic layer was washed with 50 mL of NaHCO3 solution and brine
  6. customAfter drying
  7. filtration(Na2SO4), filtration and removal of the solvent
  8. customthe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b3832f035a014ba69c903abd40c6799e
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08048895B2

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