Penicillin V → HCID 14080610, Verbindung

HRID 1657391

Reaktionsgleichung

Reaktionsgleichung von HRID 1657391
[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:23](=[O:24])[N:14]2[C@@H:15]([C:20]([OH:22])=[O:21])[C:16]([CH3:19])([CH3:18])[S:17][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(OC(C)C)=O.[C:31]1([CH:37](N)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:23](=[O:24])[N:14]2[C@@H:15]([C:20]([O:22][CH:37]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:21])[C:16]([CH3:19])([CH3:18])[S:17][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6869Penicillin VHCID 7036BenzhydrylamineHCID 10929Isopropyl nitrite

Produkt 1

HCID 14080610HCID 14080610, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6β-Phenoxyacetamido-2,2-dimethylpenam-3α-carboxylic acid (3.50 g, 10 m.moles) was added to a mixture of isopropyl nitrite (2.40 g, 27 m.moles) and diphenylmethylamine (2.21 g, 12 m.moles) in tetrahydrofuran (50 ml) at 35° and stirred for 3 hours. The solvent was removed in vacuo and the gum dissolved in chloroform (50 ml), which solution was washed with 5% sodium bicarbonate solution (50 ml) and then water (50 ml) to leave a gum of the title ester. Yield 2.11 g (40.8% based on the input penicillin acid).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe gum dissolved in chloroform (50 ml)
  3. washwhich solution was washed with 5% sodium bicarbonate solution (50 ml)

Quellen und Nachweise

ORD-Eintrag
ord-9e13c22ef111484597f2a0a324e5cfbb
Quelldatensatz
uspto-grants-1976_06
Patentnummer
US03960843

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