Triethylamine → HCID 57271406, Verbindung

HRID 1708198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1708198
C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[O:25]=[C:26]1[NH:30][CH2:29][C@@H:28]([C:31]([OH:33])=O)[O:27]1.[N+]([O-])(O)=O.[N+:38]([O:41][CH2:42][CH2:43][NH2:44])([O-:40])=[O:39]>O1CCCC1>[N+:38]([O:41][CH2:42][CH2:43][NH:44][C:31]([C@H:28]1[O:27][C:26](=[O:25])[NH:30][CH2:29]1)=[O:33])([O-:40])=[O:39]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 199401P,P-Diphenylphosphinic azideHCID 14443191(S)-2-oxooxazolidine-5-carboxylic acid

Produkt 1

HCID 57271406HCID 57271406, VerbindungAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.35 ml of triethylamine and 0.22 ml of diphenylphosphoryl azide were added, whilst ice-cooling and stirring, to a suspension of 110 mg of (5S)-2-oxooxazolidine-5-carboxylic acid (prepared by a procedure similar to that described in Preparation 3) and 170 mg of N-(2-nitrooxyethyl)amine nitrate in 10 ml of dry tetrahydrofuran, and the resulting mixture was stirred at room temperature for 6 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent. The pale yellow oil thus obtained was triturated with ethyl acetate, and the resulting precipitate was collected by filtration and washed, to give 79.8 mg of the title compound as a colorless powder, melting at 101°-103° C.

Aufarbeitung

  1. temperaturecooling
  2. customprepared by a procedure similar to
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. customthe residue was purified by column chromatography through silica gel
  5. customThe pale yellow oil thus obtained
  6. customwas triturated with ethyl acetate
  7. filtrationthe resulting precipitate was collected by filtration
  8. washwashed

Quellen und Nachweise

ORD-Eintrag
ord-10cdcd13b9424014857b9bba4fb194d9
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05356918

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