N-Methylpiperidine → 6(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

HRID 1679626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1679626
Cl.CN1CCCCC1.[C:9]1([C:15]([NH:28][CH:29]2[C:39](=[O:40])[N:31]3[CH:32]([C:37]#[N:38])[C:33]([CH3:36])([CH3:35])[S:34][C@H:30]23)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N-:41]=[N+:42]=[N-:43].[Na+].CN1CCCCC1>C(O)C.O>[C:9]1([C:15]([NH:28][CH:29]2[C:39](=[O:40])[N:31]3[CH:32]([C:37]4[NH:43][N:42]=[N:41][N:38]=4)[C:33]([CH3:36])([CH3:35])[S:34][C@H:30]23)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 12291N-MethylpiperidineHCID 33557Sodium AzideHCID 205378Piperidine, 1-methyl-, hydrochloride (1:1)HCID 70604455HCID 70604455, Verbindung

Produkt 1

HCID 1784319216(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
53 °C

Versuchsvorschrift

A mixture of dry N-methylpiperidine hydrochloride (8.14 g., 0.06 mole) anhydrous ethanol free chloroform (180 ml.), 6-triphenylmethylamino-2,2-dimethyl-3-cyanopenam (13.2g., 0.03 mole), finely powdered sodium azide (3.9 g., 0.06 mole) and N-methylpiperidine (8.9 g., 0.09 mole) is heated to 53° C. (internal temperature) for 80 minutes. It is then cooled to room temperature and diluted with ethanol free chloroform (750 ml.) and water (800 ml.). It is thoroughly shaken, the chloroform phase separated and washed successively with 1.5N HCl (1 × 1000 ml.) and water (1 × 800 ml.). The chloroform solution is filtered through anhydrous sodium sulfate and then concentrated under reduced pressure to about 300 ml. White crystals separate. The concentrate is diluted with hexane (350 ml.) and filtered after 15 minutes. The crystalline product is washed with hexane and dried in air for 15 minutes followed by drying under vacuum at 56° C. for 1 hour. Yield = 7.66 g. (52.9%).

Aufarbeitung

  1. temperatureIt is then cooled to room temperature
  2. customthe chloroform phase separated
  3. washwashed successively with 1.5N HCl (1 × 1000 ml.) and water (1 × 800 ml.)
  4. filtrationThe chloroform solution is filtered through anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure to about 300 ml
  6. customWhite crystals separate
  7. additionThe concentrate is diluted with hexane (350 ml.)
  8. filtrationfiltered after 15 minutes
  9. washThe crystalline product is washed with hexane
  10. customdried in air for 15 minutes
  11. customby drying under vacuum at 56° C. for 1 hour

Quellen und Nachweise

ORD-Eintrag
ord-3350da077b3741dd9bc11fc74d118ef8
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04081455

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