Benzyl Alcohol → 5-(Phenylmethyl) hydrogen D-glutamate

HRID 1526673Notes

Reaction equation

HRID 1526673 reaction equation
[NH2:1][C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.B(F)(F)F.CCOCC.C(N(CC)CC)C>C1COCC1>[NH2:1][C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[O:7][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 244Benzyl Alcohol2×HCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 23327D-Glutamic Acid

Product 1

HCID 69946245-(Phenylmethyl) hydrogen D-glutamateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 29.1 g (1.0 eq) H-D-Glu-OH in 205.6 mL (10.0 eq) benzyl alcohol which was stirred at r.t, 47.7 mL (2.0 eq) boron trifluoride etherate solution was added slowly, and 10 min later, all of the substrate was dissolved. The reaction was completed in 15 h, 616.8 mL (3 times of the volume of benzyl alcohol) THF was added, stirred and 55.1 mL (2.0 eq) triethylamine was added slowly. A large number of white viscous precipitate precipitated. The THF was removed under reduced pressure; the residue was cooled, after adding the proper amount of the AcOEt, the viscous precipitate turned to powder. 36.6 g target compound was obtained with yield of 78% after filtration and drying. m.p.=174˜176° C.

Workup

  1. additionwas added slowly
  2. dissolution10 min later, all of the substrate was dissolved
  3. customA large number of white viscous precipitate precipitated
  4. customThe THF was removed under reduced pressure
  5. temperaturethe residue was cooled
  6. additionafter adding the proper amount of the AcOEt
  7. custom36.6 g target compound was obtained with yield of 78%
  8. filtrationafter filtration
  9. customdrying

Sources & evidence

ORD record
ord-f02a5ead25df4179a479c1344a3d55e2
Source dataset
uspto-grants-2015_07
Patent number
US09085605B2

Reaction notes

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