Sodium Hydroxide → HCID 86653822, compound

HRID 1972184Notes

Reaction equation

HRID 1972184 reaction equation
[C:1]([NH:4][C@@H:5]([CH2:11][CH2:12][CH:13]([Br:17])[CH2:14][CH2:15][CH3:16])[C:6]([O:8]CC)=[O:7])(=[O:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([NH:4][CH:5]([CH2:11][CH2:12][CH:13]([Br:17])[CH2:14][CH2:15][CH3:16])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86653823HCID 86653823, compound

Product 1

HCID 86653822HCID 86653822, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl(S)-2-(N-acetylamino)-5-bromooctanate (3.9 g) was dissolved in EtOH and 12.7 ml (1 eq) of 1N NaOH was added every 1 hour in the total amount of 50.8 ml (4 eq), followed by stirring overnight. After concentration, the aqueous layer was washed by liquid separation using diethylether. The pH of the aqueous layer was adjusted to about 1 to 2 using 1N HCl, followed by extraction with diethylether. The diethylether layer was washed with brine and dehydrated over sodium sulfate. After concentration, 3.9 g (86.3%) of 2-(N-acetylamino)-5-bromooctanoic acid was obtained as a white solid.

Workup

  1. concentrationAfter concentration
  2. washthe aqueous layer was washed by liquid separation
  3. extractionfollowed by extraction with diethylether
  4. washThe diethylether layer was washed with brine
  5. concentrationAfter concentration

Sources & evidence

ORD record
ord-eefa4640b32b475ca963da8d98f097a4
Source dataset
uspto-grants-2013_04
Patent number
US08431738B2

Reaction notes

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