3-(2-Hydroxy-ethylidene)-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester(benzyl calvunlanate) → Clavulanic Acid

HRID 324261

Reaktionsgleichung

Reaktionsgleichung von HRID 324261
[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)C.[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

4

Edukt 1

HCID 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 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Benzyl clavulanate (100 mgs) in ethanol (5 ml) was hydrogenated over 10% Pd/C (30 mgs) for 45 minutes at ambient temperature and atmospheric pressure. The catalyst was filtered, washed with ethanol and the combined filtrates were evaporated in vacuo to give clavulanic acid as an unstable, viscous oil (58 mgs). N.m.r. (C5D5N): 3.05(d,1,J=18 Hz), 3.60(dd,1,J1=18 Hz, J2=2.5 Hz), 4.75(d,2,J=7.5 Hz), 5.58(t,1,J=7.5 Hz),5.66 (S,1), 6.0δ(d,1,J=2.5 Hz).

Aufarbeitung

  1. filtrationThe catalyst was filtered
  2. washwashed with ethanol
  3. customthe combined filtrates were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e657a547ac0a4bedab66b3ebeb614482
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218380B1

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