Sodium Hydroxide → HCID 54390455, compound

HRID 127840Notes

Reaction equation

HRID 127840 reaction equation
Cl.C1(OC(=O)[C@H](CCCCN)N[C:16](=[O:38])[C@H:17]([CH2:34][CH:35]([CH3:37])[CH3:36])[NH:18][C:19](=[O:33])[C@H:20]([CH:30]([CH3:32])[CH3:31])[NH:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)C2C(=CC=CC=2)C=CC=1.[OH-:45].[Na+]>CO>[C:22]([NH:21][C@H:20]([C:19]([NH:18][C@H:17]([C:16]([OH:38])=[O:45])[CH2:34][CH:35]([CH3:36])[CH3:37])=[O:33])[CH:30]([CH3:31])[CH3:32])(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70566515HCID 70566515, compound

Product 1

HCID 54390455HCID 54390455, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 150 ml of methanol was dissolved 5.0 g of the above ester, and 20 ml of 1N sodium hydroxide solution was added to the solution. The mixture was stirred at room temperature for 8 hrs. The reaction mixture was concentrated at a low temperature, after which ethyl acetate and distilled water were added to the residue. The resulting mixture was shaken, and the aqueous layer was separated and made weakly acidic with 10% hydrochloric acid solution. The oily substance thus precipitated was extracted with ethyl acetate, and the extract was washed with water and dried over anhydrous magnesium sulfate, and thereafter evaporated under reduced pressure to remove the solvent, thereby obtaining 3.0 g (yield 65%) of a colorless oily substance of N-benzoyl-L-valyl-L-leucine.

Workup

  1. additionwas added to the solution
  2. concentrationThe reaction mixture was concentrated at a low temperature
  3. distillationafter which ethyl acetate and distilled water
  4. additionwere added to the residue
  5. stirringThe resulting mixture was shaken
  6. customthe aqueous layer was separated
  7. customThe oily substance thus precipitated
  8. extractionwas extracted with ethyl acetate
  9. washthe extract was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated under reduced pressure
  12. customto remove the solvent

Sources & evidence

ORD record
ord-edfcff491d234780b5e2cf47c76295da
Source dataset
uspto-grants-1981_03
Patent number
US04257940

Reaction notes

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