Benzyl Bromide → D-leucic acid benzyl ester

HRID 233672

Reaction equation

HRID 233672 reaction equation
O1CCCC1.[C:6]([OH:14])(=[O:13])[C@@H:7]([CH2:9][CH:10]([CH3:12])[CH3:11])[OH:8].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(N(CC)CC)C>[CH2:15]([O:13][C:6](=[O:14])[C@@H:7]([CH2:9][CH:10]([CH3:12])[CH3:11])[OH:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 439960(R)-2-hydroxy-4-methylpentanoic acid

Product 1

HCID 9991100D-leucic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 150 ml of tetrahydrofurane of 14.50 of D-leucic acid, 15.2 g of triethylamine and then 14.4 ml of benzyl bromide are added, and the solution was stirred for 3 hours while refluxing. The insoluble matter produced from the reaction solution was filtered off, and the filtrate was concentrated in vacuo. The obtained residue was dissolved and extracted in 150 ml of ethyl acetate. The ethyl acetate layer was washed twice with saturated bicarbonate water, twice with 1N hydrochloric acid, and twice with saturated brine sequentially, and dried over sodium sulfate anhydride, and concentrated in vacuo. The obtained oily residue was dried, and the captioned compound was obtained. Yield: 18.34 g.

Workup

  1. temperaturewhile refluxing
  2. customThe insoluble matter produced from the reaction solution
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe obtained residue was dissolved
  6. extractionextracted in 150 ml of ethyl acetate
  7. washThe ethyl acetate layer was washed twice with saturated bicarbonate water, twice with 1N hydrochloric acid
  8. dry with materialtwice with saturated brine sequentially, and dried over sodium sulfate anhydride
  9. concentrationconcentrated in vacuo
  10. customThe obtained oily residue was dried
  11. customthe captioned compound was obtained

Sources & evidence

ORD record
ord-ec3d3fd529934f85b7a05b26f0e52b1d
Source dataset
uspto-grants-1997_01
Patent number
US05594006

Linked notes

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