Benzyl Bromide → D-leucic acid benzyl ester

HRID 1464368Notes

Reaction equation

HRID 1464368 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([OH:17])(=[O:16])[C@@H:10]([CH2:12][CH:13]([CH3:15])[CH3:14])[OH:11].C(N(CC)CC)C>C(OCC)(=O)C>[CH2:1]([O:17][C:9](=[O:16])[C@@H:10]([CH2:12][CH:13]([CH3:15])[CH3:14])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 439960(R)-2-hydroxy-4-methylpentanoic acid

Product 1

HCID 9991100D-leucic acid benzyl esterYield 62.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

278 g of benzyl bromide were added to a stirred solution of 215 g of D-leucic acid and 246 g of triethylamine in 2.5 l of ethy acetate. The mixture was then heated under reflux for 5 hours, cooled and filtered to remove triethylamine hydrobromide. The filtrate was washed twice with 2M hydrochloric acid, water, saturated sodium bicarbonate solution and then saturated sodium chloride solution. The organic extract was dried over magnesium sulfate and evaporated to give 225 g of D-leucic acid benzyl ester as a yellow liquid.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 5 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove triethylamine hydrobromide
  6. washThe filtrate was washed twice with 2M hydrochloric acid, water, saturated sodium bicarbonate solution
  7. extractionThe organic extract
  8. dry with materialwas dried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-2a65db725f7844339a3a8ea47ca58912
Source dataset
uspto-grants-1994_04
Patent number
US05304549

Reaction notes

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