Potassium Bromide → Clavulanic Acid

HRID 324262

Reaktionsgleichung

Reaktionsgleichung von HRID 324262
[CH2:1]1[C:4](=[O:5])[N:3]2[C@@H:6]([C:12]([O:14]CC3C=CC=CC=3)=[O:13])/[C:7](/[O:11][C@H:2]12)=[CH:8]/[CH2:9][OH:10].C(=O)(O)[O-].[Na+].[K+].[Br-]>C(O)C.O.[Pd]>[CH2:1]1[C:4](=[O:5])[N:3]2[C@@H:6]([C:12]([OH:14])=[O:13])/[C:7](/[O:11][C@H:2]12)=[CH:8]/[CH2:9][OH:10]

Komponenten

7

Edukt 3

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 99040553-(2-Hydroxy-ethylidene)-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester(benzyl calvunlanate)

Produkt 1

HCID 5280980Clavulanic Acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Benzyl clavulanate (840 mgs) in ethanol (30 ml) and water (5 ml) was hydrogenated over 10% Pd/C (267 mgs) and sodium bicarbonate (244 mgs) for 25 minutes at room temperature and atmospheric pressure. The catalyst was filtered, washed with water and ethanol and the combined filtrates were evaporated in vacuo. The product crystallised from a water-acetone mixture as microneedles (565 mgs). Recrystallisation from water-acetone gave needles which, after drying over P2O5 in vacuo for 24 hours gave the following analysis: C 41.01, 40.86; H 3.77, 3.64; N 5.68, 5.51; i.r.(KBr disc) 1785, 1700, 1620 cm−1; Nmr (D2O) 3.06 (d,1,J=18.5 Hz), 3.57 (dd,1,J1=18.5 Hz, J2=2.5 Hz), 4.15 (d,2,J=8 Hz), 5.3 (HOD), 4.9 (m), 5.71 (d,1,J=2.5 Hz).

Aufarbeitung

  1. filtrationThe catalyst was filtered
  2. washwashed with water and ethanol
  3. customthe combined filtrates were evaporated in vacuo
  4. customThe product crystallised from a water-acetone mixture as microneedles (565 mgs)
  5. customRecrystallisation from water-acetone
  6. customgave needles which
  7. dry with materialafter drying over P2O5 in vacuo for 24 hours
  8. customgave the following analysis

Quellen und Nachweise

ORD-Eintrag
ord-54767968ac974cc9bc2fa7faf14350c2
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218380B1

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