Triethylamine → HCID 18961068, compound

HRID 487966Notes

Reaction equation

HRID 487966 reaction equation
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][CH:28]([C:31]([OH:33])=O)[S: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]([CH:28]1[S:27][C:26](=[O:25])[NH:30][CH2:29]1)=[O:33])([O-:40])=[O:39]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 199401P,P-Diphenylphosphinic azideHCID 189610442-Oxo-1,3-thiazolidine-5-carboxylic acid

Product 1

HCID 18961068HCID 18961068, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.85 ml of triethylamine and 0.53 ml of diphenylphosphoryl azide were added, whilst ice-cooling, to a suspension of 0.30 g of 2-oxothiazolidine-5-carboxylic acid (prepared as described in Preparation 3) and 0.41 g of N-(2-nitrooxyethyl)amine nitrate in 10 ml of dry tetrahydrofuran, and the resulting mixture was stirred at room temperature for 2.5 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 crude crystals thus obtained were triturated with diisopropyl ether, collected by filtration and washed to give 0.40 g of the title compound as a colorless powder, melting at 114°-115° C.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. customthe residue was purified by column chromatography through silica gel
  3. customThe crude crystals thus obtained
  4. customwere triturated with diisopropyl ether
  5. filtrationcollected by filtration
  6. washwashed

Sources & evidence

ORD record
ord-4c9ecbe3fcd84802bfb73505c444ca24
Source dataset
uspto-grants-1994_03
Patent number
US05298516

Reaction notes

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