Triethylamine → (4R)-N-(2-Nitrooxyethyl)-2-oxothiazolidine-4-carboxamide

HRID 487944

Reaktionsgleichung

Reaktionsgleichung von HRID 487944
C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[O:18]=[C:19]1[NH:23][C@H:22]([C:24]([OH:26])=O)[CH2:21][S:20]1.[N+]([O-])(O)=O.[N+:31]([O:34][CH2:35][CH2:36][NH2:37])([O-:33])=[O:32]>O1CCCC1>[N+:31]([O:34][CH2:35][CH2:36][NH:37][C:24]([C@@H:22]1[CH2:21][S:20][C:19](=[O:18])[NH:23]1)=[O:26])([O-:33])=[O:32]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 72390ProcysteineHCID 76257Diethyl cyanophosphonateHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)

Produkt 1

HCID 9856101(4R)-N-(2-Nitrooxyethyl)-2-oxothiazolidine-4-carboxamideAusbeute 26,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

11.4 ml of triethylamine and 5.3 ml of diethyl cyanophosphonate were added, whilst ice-cooling, to a suspension of 4.0 g of (4R)-2-oxothiazolidine-4-carboxylic acid and 4.6 g of N-(2-nitrooxyethyl)amine nitrate in 80 ml of dry tetrahydrofuran, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was mixed with ethyl acetate. The resulting mixture was then washed with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residual brown oil thus obtained was purified by column chromatography through silica gel, using ethyl acetate as the eluent. The brown crystals thus obtained were recrystallized from ethyl acetate, to give 1.68 g of the title compound as colorless needles, melting at 130°-131° C. (with decomposition).

Aufarbeitung

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionthe residue was mixed with ethyl acetate
  3. washThe resulting mixture was then washed with a saturated aqueous solution of sodium chloride
  4. dry with materialafter which it was dried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customthe residual brown oil thus obtained
  7. customwas purified by column chromatography through silica gel
  8. customThe brown crystals thus obtained
  9. customwere recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6f9ea747fb2d4103a702fed6b8dfb096
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05298516

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