Benzyl Alcohol → L-Glutamic acid, 5-(phenylmethyl) ester

HRID 1056912Notes

Reaction equation

HRID 1056912 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CS(O)(=O)=O.O>C1(C)C=CC=CC=1>[NH2:1][C@@H:2]([CH2:3][CH2:4][C:5]([O:7][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:6])[C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 6395Methanesulfonic AcidHCID 33032L-Glutamic Acid

Product 1

HCID 122337L-Glutamic acid, 5-(phenylmethyl) ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

Glutamic acid (20 g, 0.14 mol, 1 equiv), BnOH (21.1 mls, 0.20 moles, 1.5 equiv) were dissolved in of toluene (30 ml) with stirring in a three necked RB flask. To the resultant mixture methanesulphonic acid (10.6 ml, 0.16 mol, 1.2 equiv) was added slowly whilst maintaining the temperature of the mixture at 45° C. Stirring was continued at this temperature for 2 hrs following which the mixture was cooled to 30° C. and stirred for an additional 4 hrs. Water (50 ml) was then added to the mixture and the organic phase was separated. To the aqueous phase ethanol (30 ml) was added followed by cold aq. ammonia to obtain a pH of 6.5-7. At this point a thick white precipitate was formed which could either be heated to 60° C. and stirred for 2 hrs to improve the crystallinity and then cooled to 5-10° C. or filtered at this point and washed with ethanol (2×20 ml) and water (3×20 ml). The product is then allowed to dry and used without further purification (3.45 g, 21%).

Workup

  1. stirringStirring
  2. temperaturewas cooled to 30° C.
  3. stirringstirred for an additional 4 hrs
  4. customthe organic phase was separated
  5. additionTo the aqueous phase ethanol (30 ml) was added
  6. customto obtain a pH of 6.5-7
  7. customAt this point a thick white precipitate was formed which
  8. temperaturecould either be heated to 60° C.
  9. stirringstirred for 2 hrs
  10. temperaturecooled to 5-10° C.
  11. filtrationfiltered at this point
  12. washwashed with ethanol (2×20 ml) and water (3×20 ml)
  13. customto dry
  14. customused without further purification (3.45 g, 21%)

Sources & evidence

ORD record
ord-11df88ed2ed24f51a6f706f2f62ede17
Source dataset
uspto-grants-2016_07
Patent number
US09399661B2

Reaction notes

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