Benzyl Bromide → Benzyl 6,6-dibromopenicillanate

HRID 1680827

Reaktionsgleichung

Reaktionsgleichung von HRID 1680827
[CH3:1][C:2]1([CH3:15])[S:6][C@@H:5]2[C:7]([Br:11])([Br:10])[C:8](=[O:9])[N:4]2[C@H:3]1[C:12]([OH:14])=[O:13].C(N(CC)CC)C.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C(=O)C>[CH3:1][C:2]1([CH3:15])[S:6][C@@H:5]2[C:7]([Br:11])([Br:10])[C:8](=[O:9])[N:4]2[C@H:3]1[C:12]([O:14][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:13]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 903766,6-Dibromopenicillanic acid

Produkt 1

HCID 10939285Benzyl 6,6-dibromopenicillanateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of 54 g. (0.165 mole) of 6,6-dibromopenicillanic acid in 350 ml. of N,N-dimethylacetamide was added 22.9 ml. (0.165 mole) of triethylamine and the solution was stirred for 40 minutes. Benzyl bromide (19.6 ml., 0.165 mole) was added and the resulting mixture was stirred at room temperature for 48 hours. The precipitated triethylamine hydrobromide was filtered off, and the filtrate was added to 1,500 ml. of ice-water, adjusted to pH 2. The mixture was extracted with ether, and the extracts were washed successively with saturated sodium bicarbonate, water and brine. The dried (MgSO4) ether solution was evaporated in vacuo to give an off-white solid, which was recrystallized from isopropanol. This afforded 70.0 g. (95% yield) of the title compound m.p. 75°-76° C. The IR spectrum (KBr disc) showed absorptions at 1795 and 1740 cm-1. The NMR spectrum (CDCl3) showed absorptions at 1.53 (s, 3H), 1.58 (s, 3H), 4.50 (s, 1H), 5.13 (s, 2H), 5.72 (s, 1H) and 7.37 (s, 5H) ppm.

Aufarbeitung

  1. filtrationThe precipitated triethylamine hydrobromide was filtered off
  2. additionthe filtrate was added to 1,500 ml
  3. extractionThe mixture was extracted with ether
  4. washthe extracts were washed successively with saturated sodium bicarbonate, water and brine
  5. dry with materialThe dried (MgSO4) ether solution
  6. customwas evaporated in vacuo
  7. customto give an off-white solid, which
  8. customwas recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-52fda15eda2a445e83622c34bf6e954b
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04276285

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