Sodium Chloride → 6-Amino-2,2-dimethyl-3-(2-[pivaloyloxymethyl]tetrazol-5-yl)penam hydrochloride

HRID 1448400

Reaktionsgleichung

Reaktionsgleichung von HRID 1448400
N1C2C(=CC=CC=2)C=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12].C1(CC([NH:26][CH:27]2[C:48](=[O:49])[N:29]3[CH:30]([C:35]4[N:36]=[N:37][N:38]([CH2:40][O:41][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[N:39]=4)[C:31]([CH3:34])([CH3:33])[S:32][C@H:28]23)=O)C=CC=CC=1.C(OC(C)C)(C)C.CC(C)=O.[Cl-].[Na+]>O.C(O)CC.C(Cl)(Cl)Cl>[ClH:12].[NH2:26][CH:27]1[C:48](=[O:49])[N:29]2[CH:30]([C:35]3[N:36]=[N:37][N:38]([CH2:40][O:41][C:42](=[O:47])[C:43]([CH3:45])([CH3:44])[CH3:46])[N:39]=3)[C:31]([CH3:33])([CH3:34])[S:32][C@H:28]12

Komponenten

9

Edukt 5

HCID 5234Sodium ChlorideHCID 7047QuinolineHCID 24819Phosphorus pentachlorideHCID 22221350Acetone diisopropyl etherHCID 706049076-(2-Phenylacetamido)-2,2-dimethyl-3-(2-[pivaloyloxymethyl]tetrazol-5-yl)penam

Produkt 1

HCID 706057856-Amino-2,2-dimethyl-3-(2-[pivaloyloxymethyl]tetrazol-5-yl)penam hydrochlorideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 10311-PropanolLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

To a stirred solution of 0.932 g. (7.21 m mole) of quinoline in 8.0 ml. of chloroform is added 0.840 g. (4.05 m mole) of phosphorus pentachloride. The suspension is cooled to -15° C., and then 1.81 g. (3.84 m mole) of 6-(2-phenylacetamido)-2,2-dimethyl-3-(2-[pivaloyloxymethyl]tetrazol-5-yl)penam is added. Stirring is continued for a further 30 minutes, at ca. -5° C., and then 2.15 g. (35.7 m mole) of n-propanol is added. Stirring is continued for a further 30 minutes, again at ca. -5° C., and then 25 ml. of 90:10 isopropyl ether-acetone is added, followed immediately by a solution of 1.35 g. of sodium chloride in 6.02 ml. of water. The temperature rises to 15° C. and then it is lowered again to -15° C. The precipitate which has formed is filtered off and dried, giving 1.33 g. (88% yield) of 6-amino-2,2-dimethyl-3-(2-[pivaloyloxymethyl]tetrazol-5-yl)penam hydrochloride. The infrared spectrum (KBr disc) shows absorptions at 1785 cm-1 (β-lactam) and 1750 cm-1 (ester). The NMR spectrum (DMSO-d6) shows absorptions at 6.70 ppm (singlet, 2H, pivaloyloxy methylene hydrogens), 5.75 ppm (doublet, 1H, C-5 hydrogen), 5.50 ppm (singlet, 1H, C-3 hydrogen), 5.70 ppm (doublet, 1H, C-6 hydrogen), 1.75 ppm (singlet, 3H, C-2 methyl hydrogens), 1.20 ppm (singlet, 9H, t-butyl hydrogens) and 1.10 ppm (singlet, 3H, C-2 methyl hydrogens).

Aufarbeitung

  1. stirringStirring
  2. waitis continued for a further 30 minutes, again at ca. -5° C.
  3. customrises to 15° C.
  4. customis lowered again to -15° C
  5. customThe precipitate which has formed
  6. filtrationis filtered off
  7. customdried
  8. customgiving 1.33 g

Quellen und Nachweise

ORD-Eintrag
ord-f8ce3170218a489abaa4f0bb8bbe9e29
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04179511

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