Sodium ethoxide → HCID 86743472, compound

HRID 2352336Notes

Reaction equation

HRID 2352336 reaction equation
[O-]CC.[Na+].[CH2:5]([O:7][C:8](=[O:22])[CH2:9][C:10]([NH:12][C@@H:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:14]([O:16]C)=O)=[O:11])[CH3:6].[Na]>C(O)C>[OH:16][C:14]1[C@H:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[NH:12][C:10](=[O:11])[C:9]=1[C:8]([O:7][CH2:5][CH3:6])=[O:22]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 14651684HCID 14651684, compound

Product 1

HCID 86743472HCID 86743472, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 123.1 g (0.38 mol, 2.5% less than theory) of "21 weight percent sodium ethoxide in ethanol" (Aldrich Chemical Co.) is added all at once to a solution of 101 g (0.39 mol) of (S)-2-[(3-ethoxy-1,3-dioxopropyl)amino]-4-methylpentanoic acid, methyl ester in 200 ml of absolute ethanol. There is no heat of reaction. After about two minutes a solid separates (sodium salt of product) and the mixture becomes thick. The mixture is heated at reflux for 30 minutes (complete solution) and then cooled to room temperature (solid reappears). The solid is collected by filtration and washed with diethyl ether. The resulting cake is dissolved by adding to 1 L of ice water with stirring, 400 ml of 1 N hydrochloric acid solution is added and the separated solid is filtered, washed with water and dried one hour under suction to afford (S)-2,5-dihydro-4-hydroxy-5-(2-methylpropyl)-2-oxo-1H-pyrrole-3-carboxylic acid, ethyl ester as a moist solid which is used in the next steps without further purification. TLC (acetic acid, methanol, chloroform, silica gel, iodine) Rf =0.6.

Workup

  1. temperatureno heat of reaction
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 30 minutes (complete solution)
  4. filtrationThe solid is collected by filtration
  5. washwashed with diethyl ether
  6. dissolutionThe resulting cake is dissolved
  7. additionby adding to 1 L of ice water
  8. addition400 ml of 1 N hydrochloric acid solution is added
  9. filtrationthe separated solid is filtered
  10. washwashed with water
  11. customdried one hour under suction

Sources & evidence

ORD record
ord-c39a97dafd7748a3b768485735d6da7a
Source dataset
uspto-grants-1989_10
Patent number
US04876343

Reaction notes

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