Triethylamine → HCID 86755208, compound

HRID 1636575Notes

Reaction equation

HRID 1636575 reaction equation
[Cl-].[OH:2][NH3+:3].C(N(CC)CC)C.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([C@@:19]2([CH3:52])[C:23](=[O:24])[N:22]([CH2:25][C:26]([O:28][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)=[O:27])[C:21](=[O:40])[N:20]2[CH2:41][C:42]2[CH:51]=[CH:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH:43]=2)=[CH:15][CH:14]=1)#[N:12]>C(O)C>[NH2:12][C:11](=[N:3][OH:2])[C:13]1[CH:18]=[CH:17][C:16]([C@@:19]2([CH3:52])[C:23](=[O:24])[N:22]([CH2:25][C:26]([O:28][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)=[O:27])[C:21](=[O:40])[N:20]2[CH2:41][C:42]2[CH:51]=[CH:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH:43]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21645Hydroxylamine HClHCID 54184405HCID 54184405, compound

Product 1

HCID 86755208HCID 86755208, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.67 g (24 mmol) of hydroxylammonium chloride and 5.04 ml (36 mmol) of triethylamine were added to a solution of 6.64 g (12 mmol) of 2-naphthylmethyl ((S)-4-(4-cyanophenyl)-3-(2-naphthylmethyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)acetate in 120 ml of absolute ethanol and the mixture was heated under reflux for 2.5 h. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The phases were separated and the water phase was extracted with ethyl acetate. The combined organic phases were washed with water and dried over magnesium sulfate. After filtration, the solvent was removed in vacuo and 6.08 g (86%) of the title compound were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe phases were separated
  6. extractionthe water phase was extracted with ethyl acetate
  7. washThe combined organic phases were washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bb551054fa764dfa99697000bc1ed317
Source dataset
uspto-grants-2000_03
Patent number
US06034238

Reaction notes

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