Triethylamine → HCID 57271406, compound

HRID 1708198Notes

Reaction equation

HRID 1708198 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][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]

Participants

6

Reactant 4

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

Product 1

HCID 57271406HCID 57271406, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-10cdcd13b9424014857b9bba4fb194d9
Source dataset
uspto-grants-1994_10
Patent number
US05356918

Reaction notes

Loading…