Triethylamine → HCID 19091486, compound

HRID 487946Notes

Reaction equation

HRID 487946 reaction equation
C(N(CC)CC)C.Cl.CN(CCCN=C=NCC)C.[O:20]=[C:21]1[NH:25][CH:24]([C:26]([OH:28])=O)[CH:23]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[S:22]1.[N+]([O-])(O)=O.[N+:39]([O:42][CH2:43][CH2:44][NH2:45])([O-:41])=[O:40]>CN(C)C=O>[N+:39]([O:42][CH2:43][CH2:44][NH:45][C:26]([CH:24]1[CH:23]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[S:22][C:21](=[O:20])[NH:25]1)=[O:28])([O-:41])=[O:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13854700HCID 13854700, compound

Product 1

HCID 19091486HCID 19091486, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.07 ml of triethylamine and 90 mg of 1-(N,N-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added, whilst ice-cooling and stirring, to a solution of 105 mg of 2-oxo-5-phenylthiazolidine-4-carboxylic acid and 79.5 mg of N-(2-nitrooxyethyl)amine nitrate in 10 ml of dry N,N-dimethylformamide, and the resulting mixture was stirred at room temperature overnight. 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 washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was distilled off and the residual yellow oil was triturated with diethyl ether. The crystals which precipitated were collected by filtration and purified by column chromatography through silica gel, using a 40:1 by volume mixture of methylene chloride and methanol as the eluent, to give 34 mg of the title compound as pale yellow crystals, melting at 139°-140° C.

Workup

  1. temperaturecooling
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. additionthe residue was mixed with ethyl acetate
  4. washThe resulting mixture was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residual yellow oil was triturated with diethyl ether
  8. customThe crystals which precipitated
  9. filtrationwere collected by filtration
  10. custompurified by column chromatography through silica gel
  11. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-12111352038345f7bf6b7812945bad0e
Source dataset
uspto-grants-1994_03
Patent number
US05298516

Reaction notes

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